- A One-Pot Synthesis of α,β-Unsaturated Esters From Esters
-
A convenient method for reductive Horner–Wadsworth–Emmons (HWE) olefination is described. The E-selective HWE homologation of various esters to α,β-unsaturated esters was readily achieved and gave the desired products in good-to-moderate yields under mild conditions. The one-pot reaction proceeds through an in situ generated aldehyde, formed via the partial reduction of an ester with lithium diisobutyl-t-butoxyaluminum hydride. The formation of cyclized metal acetal and subsequent decompose to the aldehyde for the olefination was found to be a crucial step in this C2-carbon homologation protocol.
- Hong, Chang Whee,Lee, Yong Jin,An, Duk Keun
-
p. 1121 - 1125
(2021/06/01)
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- Synthesis and Biological Evaluation of Hoshionolactam-Based Compounds
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In search of novel antitrypanosomal agents based on hoshinolactam (IC50=3.9 nM), we disclose the synthesis and biological evaluations of 14 different analogues of the natural product using combinations of different acids and lactams. Antitrypanosomal activity assays revealed that the synthesized analogues were less potent than the parent natural product.
- Elizebath, Drishya,Jachak, Gorakhnath R.,Reddy, D. Srinivasa,Shanmugam, Dhanasekaran,Shukla, Anurag
-
p. 2212 - 2218
(2021/07/22)
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- Phosphorus-recycling wittig reaction: Design and facile synthesis of a fluorous phosphine and its reusable process in the wittig reaction
-
This study shows that phosphorus sources can be recycled using the appropriate fluorous phosphine in the Wittig reaction. The designed fluorous phosphine, which has an ethylene spacer between its phosphorus atom and the perfluoroalkyl group, was synthesized from air-stable phosphine reagents. The synthesized phosphine can be used for the Wittig reaction process to obtain various alkenes in adequate yields and stereoselectivity. The concomitantly formed fluorous phosphine oxide was extracted from the reaction mixture using a fluorous biphasic system. The fluorous phosphine was regenerated by reducing the fluorous phosphine oxide with diisobutylaluminum hydride. Finally, a series of gram scale phosphorus recycling processes were performed, which included the Wittig reaction, separation, reduction, and reuse.
- Yamamoto, Yuki,Kawaguchi, Shin-Ichi,Nishimura, Misaki,Sato, Yuki,Shimada, Yoshihisa,Tabuchi, Akihiro,Nomoto, Akihiro,Ogawa, Akiya
-
p. 14684 - 14696
(2020/11/30)
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- CuBr2-catalyzed diastereoselective allylation: Total synthesis of decytospolides A and B and their C6-epimers
-
An efficient CuBr2-catalyzed diastereoselective allylation of a cyclic hemiacetal with allyltrimethylsilane as a nucleophile has been developed. The protocol offers a cost effective, protecting group tolerant, and operationally simple approach to 2,6-trans-disubstituted tetrahydropyran with excellent diastereoselectivity. Furthermore, the application of this methodology has been demonstrated in the total synthesis of decytospolides A and B and their C6-epimers.
- Choudhury, Utkal Mani,Mallampudi, N. Arjunreddy,Mohapatra, Debendra K.,Padhi, Birakishore,Reddy, G. Sudhakar
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p. 2685 - 2695
(2020/04/17)
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- Stereoselective Synthesis of C1–C7 and C6–C22 Fragments of Phostriecin, Goniothalamines, and Their Analogues
-
The stereoselective synthesis of two fragments (C1–C7 and C6–C22) of the anti-tumor agent phostriecin has been achieved. The chiral hydroxy-vinyl-δ-lactone building block (fragment C1–C7) was subsequently utilized for the synthesis of 5-hydroxygoniothalamin, 5-acetoxygoniothalamin, and their derivatives.
- Purushotham Reddy,Vasudeva Reddy,Sabitha, Gowravaram
-
p. 4389 - 4399
(2018/09/11)
-
- Synthesis of α,β-unsaturated aldehydes as potential substrates for bacterial luciferases
-
Bacterial luciferase catalyzes the monooxygenation of long-chain aldehydes such as tetradecanal to the corresponding acid accompanied by light emission with a maximum at 490?nm. In this study even numbered aldehydes with eight, ten, twelve and fourteen carbon atoms were compared with analogs having a double bond at the α,β-position. These α,β-unsaturated aldehydes were synthesized in three steps and were examined as potential substrates in vitro. The luciferase of Photobacterium leiognathi was found to convert these analogs and showed a reduced but significant bioluminescence activity compared to tetradecanal. This study showed the trend that aldehydes, both saturated and unsaturated, with longer chain lengths had higher activity in terms of bioluminescence than shorter chain lengths. The maximal light intensity of (E)-tetradec-2-enal was approximately half with luciferase of P. leiognathi, compared to tetradecanal. Luciferases of Vibrio harveyi and Aliivibrio fisheri accepted these newly synthesized substrates but light emission dropped drastically compared to saturated aldehydes. The onset and the decay rate of bioluminescence were much slower, when using unsaturated substrates, indicating a kinetic effect. As a result the duration of the light emission is doubled. These results suggest that the substrate scope of bacterial luciferases is broader than previously reported.
- Brodl, Eveline,Ivkovic, Jakov,Tabib, Chaitanya R.,Breinbauer, Rolf,Macheroux, Peter
-
p. 1487 - 1495
(2017/02/18)
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- Asymmetric Total Syntheses of Two Possible Diastereomers of Gliomasolide e and Its Structural Elucidation
-
The first total syntheses of two possible diastereomers of gliomasolide E, a 14-membered macrolides isolated from the marine sponge Phakellia fusca Thiele, which was collected from the South China Sea, is reported. Highlights of the synthesis include macrolactonization through intramolecular Horner-Wadsworth-Emmons olefination, Yamaguchi-Hirao alkynylation, and base-induced elimination reactions for propargyl alcohol synthesis as the key reactions. Detailed comparison of their 1H and 13C NMR (1D and 2D NMR data) and specific rotation with those of the natural product revealed that the absolute stereochemistry of gliomasolide E should be (2E,5R,7R,9R,13R).
- Reddy, Ramidi Gopal,Venkateshwarlu, Ravula,Ramakrishna, Kallaganti V. S.,Yadav, Jhillu S.,Mohapatra, Debendra K.
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p. 1053 - 1063
(2018/06/18)
-
- Selective Hydrogenation of Functionalized Alkynes to (E)-Alkenes, Using Ordered Alloys as Catalysts
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Intermetallic Pd3Pb acts as a highly selective alkyne semihydrogenation catalyst that is greatly superior to the conventional Lindlar catalyst. Density functional theory (DFT) calculations demonstrate an ideal adsorption property of Pd3Pb, where the surface holds alkynes while releasing alkenes. A tandem catalytic system that is comprised of Pd3Pb/SiO2 for alkyne semihydrogenation and RhSb/SiO2 for alkene isomerization allows one-pot (E)-alkene synthesis from a functionalized alkyne, which is the first success using heterogeneous catalysts. A variety of functionalized alkynes with aldehyde, ketone, carboxylic acid, and ester moieties are hydrogenated into the corresponding (E)-alkene in good to excellent yields under 1 atm H2 at room temperature.
- Furukawa, Shinya,Komatsu, Takayuki
-
p. 2121 - 2125
(2016/03/15)
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- Oxidative carbon-carbon bond cleavage is a key step in spiroacetal biosynthesis in the fruit fly Bactrocera cacuminata
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The early steps of spiroacetal biosynthesis in the fruit fly Bactrocera cacuminata (Solanum fly) have been investigated using a series of deuterium-labeled, oxygenated fatty acid like compounds. These potential spiroacetal precursors were administered to male flies, and their volatile emissions were analyzed for specific deuterium incorporation by GC/MS. This has allowed the order of early oxidative events in the biosynthetic pathway to be determined. Together with the already well-established later steps, the results of these in vivo investigations have allowed essentially the complete delineation of the spiroacetal biosynthetic pathway, beginning from products of primary metabolism. A fatty acid equivalent undergoes a series of enzyme-mediated oxidations leading to a trioxygenated fatty acid like species that includes a vicinal diol. This moiety then undergoes enzyme-mediated oxidative carbon-carbon bond cleavage as the key step to generate the C9 unit of the final spiroacetal. This is the first time such an oxidative transformation has been reported in insects. A final hydroxylation step is followed by spontaneous spiro-cyclization. This distinct pathway adds further to the complexity and diversity of biosynthetic pathways to spiroacetals.
- Singh, Arti A.,Rowley, Jessica A.,Schwartz, Brett D.,Kitching, William,De Voss, James J.
-
p. 7799 - 7821
(2015/03/18)
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- Microwave-assisted convenient synthesis of α,β-unsaturated esters and ketones via aldol-adduct elimination
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Various fluorinated 3-oxo ester/1,3-diketones were reacted with carbonyl compounds, in presence of piperidine and under microwave irradiation, to afford (E)-α,β-unsaturated esters and ketones in good yields. The systematic study reveals that the reaction proceeded through the formation of aldol adduct. The method provides a new and simple way for C,C bond formations. Copyright
- Suman, Pathi,Nageswara Rao, Rayala,China Raju, Bhimapaka
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p. 1548 - 1559
(2013/09/02)
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- A continuous homologation of esters: An efficient telescoped reduction-olefination sequence
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A continuous protocol for the two-carbon homologation of esters to α,β-unsaturated esters is described. This multireactor homologation telescopes an ester reduction, phosphonate deprotonation, and Horner-Wadsworth-Emmons olefination, thus converting a three-operation procedure into a single, uninterrupted system that eliminates the need for isolation or purification of the aldehyde intermediates. The homologated products are obtained in high yield and selectivity.
- Webb, Damien,Jamison, Timothy F.
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supporting information; experimental part
p. 2465 - 2467
(2012/07/01)
-
- Olefination reactions using tetraarylphosphonium (TAP)-supported phosphorus ylides
-
Tetraarylphosphonium (TAP)-supported phosphorus ylides were prepared and used in copper-catalyzed olefination reactions with diazo compounds to produce conjugated esters, amides, and phosphonates. The TAP-phosphine oxide can easily be separated from the alkene product, recycled, and reused. Georg Thieme Verlag Stuttgart ? New York.
- Lebel, Helene,Davi, Michael,Roy, Marie-Noelle,Zeghida, Walid,Charette, Andre B.
-
experimental part
p. 2275 - 2280
(2011/09/15)
-
- New and facile approach for the synthesis of (E)-α,β-unsaturated esters and ketones
-
A general and practical synthesis of (E)-α,β-unsaturated esters and ketones was achieved by the reaction of carbonyl compounds with ethyl-4,4,4-trifluoroacetoacetate and trifluoro-substituted 1,3-diketones in the presence of piperidine in dichloromethane at raoom temperature (≈40°C) with excellent stereoselectivity (see scheme).
- China Raju, Bhimapaka,Suman, Pathi
-
supporting information; experimental part
p. 11840 - 11842
(2011/01/12)
-
- First stereoselective total synthesis and anticancer activity of new amide alkaloids of roots of pepper
-
The first stereoselective total synthesis of new natural amide alkaloids 1-3 have been achieved from commercially available starting materials. Wittig olefination, Sharpless asymmetric dihydroxylation, epoxidation, a trans regioselective opening of 2,3-epoxy alcohol, Horner-Wadsworth-Emmons (HWE) olefination and amide coupling are the key steps. The amide alkaloids 1-3 are evaluated for their anticancer activity against colon (HT-29), breast (MCF-7) and lung (A-549) human cancer cell lines for the first time.
- Srinivas,Sai Pavan Kumar,China Raju,Jayathirtha Rao,Naidu,Ramakrishna,Diwan, Prakash V.
-
scheme or table
p. 5915 - 5918
(2010/04/29)
-
- A facile chemoenzymatic approach to chiral non-racemic β-alkyl-γ-amino acids and 2-alkylsuccinic acids. A concise synthesis of (S)-(+)-Pregabalin
-
Both enantiomerically pure antipodes of GABA analogues were prepared as hydrochloride salts, by enzymatic kinetic resolution of their precursors ethyl 2-(nitromethyl)alkanoates. These latter compounds can be easily transformed into enantiomerically pure 2-alkylsuccinic acids by a Nef reaction followed by oxidation. Interestingly, this reaction was particularly easy for the neopentyl derivative (S)-(+)-7d, which underwent conversion into its corresponding succinic acid derivative (S)-(-)-8d in buffered solution. The absolute configurations of the main compounds of interest involved are given, together with their CD spectra.
- Felluga, Fulvia,Pitacco, Giuliana,Valentin, Ennio,Venneri, Cesare Daniele
-
p. 945 - 955
(2008/09/21)
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- Phosphazene base-catalyzed condensation of trimethylsilylacetate with carbonyl compounds
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The t-Bu-P4 base was found to be an excellent catalyst for the condensation of trimethylsilylacetate or trimethylacetonitrile with carbonyl compounds to form functionalized alkenes and β-enaminoesters were also synthesized by the condensation with formanilides. The Royal Society of Chemistry 2006.
- Kobayashi, Koji,Ueno, Masahiro,Kondo, Yoshinori
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p. 3128 - 3130
(2008/09/20)
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- METHOD FOR THE PRODUCTION OF OLEFINS FROM CARBONYL COMPOUNDS
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A method for the production of a,?-unsaturated compounds of general formula (I) is disclosed, where R1 and R2 independently = H, substituted or unsubstituted alkyl or aryl, R3 = H, substituted or unsubstituted alkyl or aryl, or a functional group such as OR4, NR5R6, SR7, where R4, R5, R6 and R7 = common substituents in particular, alkyl- and/or aryl groups, or halogen, EWG = an electron withdrawing group such as for example, CO2H, CO2R8, CONR9R10, COSR11, CN, NO2, SO2R12, CHO, COR13, etc. where R8, R9, R10, R11, R12 and R13 = common substituents, in particular, alkyl- and/or aryl groups, in which a carbonyl compound of formula (II), in which R1 and R2 are as defined above, is reacted with a carboxylic acid of formula (III) in the presence of an amine or with the same acid generated in situ by the addition of an acid to the salt thereof in which R3 and EWG are as defined above. Under mild reaction conditions unsaturated esters with high (E)-stereoselectivity are obtained. The reaction typically occurs at room temperature or lower without particular requirements such as inert gas, exclusion of humidity, heat etc. CO2 and water are obtained as the only by-products.
- -
-
Page/Page column 8
(2008/06/13)
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- Ethyl (benzothiazol-2-ylsulfonyl)acetate: A new reagent for the stereoselective synthesis of α,β-unsaturated esters from aldehydes
-
The title reagent engaged in the modified Julia olefination with aldehydes under mild reaction conditions (DBU, CH2Cl2, rt or -78°C) to yield α,β-unsaturated esters; aryl aldehydes and aliphatic aldehydes possessing significant chain branching elements gave trans alkene products with high stereoselectivity (E : Z up to >98 : 2), while straight chain aliphatic aldehydes gave cis products preferentially (Z : E up to 92 : 8). The Royal Society of Chemistry 2095.
- Blakemore, Paul R.,Ho, Danny K.H.,Nap, W. Mieke
-
p. 1365 - 1368
(2007/10/03)
-
- One-pot dehydrogenation of carboxylic acid derivatives to α,β-unsaturated carbonyl compounds under mild conditions
-
Carboxylic acid derivatives such as N-acyl-2-oxazolidones, δ-lactones, and δ-lactams were smoothly dehydrogenated to the corresponding α,β-unsaturated carbonyl compounds in one-pot manner at -78°C just by treating their lithium enolates with N-tert- butyl
- Matsuo, Jun-Ichi,Aizawa, Yayoi
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p. 407 - 410
(2007/10/03)
-
- Stereoselective synthesis of naturally occurring unsaturated amide alkaloids by a modified Ramberg-Baecklund reaction
-
A convenient and rapid approach for the synthesis of naturally occurring unsaturated amide alkaloids 1a-1n by the recently developed one-flask Ramberg-Baecklund reaction is described. The starting material was alcohol 3, which was transformed into thiolacetate 4 using the Mitsunobu reaction. In situ cleavage of acetyl moiety of 4, followed by alkylation of the resulting thiol with appropriate chloroacetamide 5, provided the sulfide 6. Oxidation of sulfide 6 gave the corresponding sulfone 2. Treatment of the sulfone 2 with the dibromodifluoromethane in the presence of alumina-supported potassium hydroxide in dichloromethane solution afforded unsaturated amide alkaloids 1a-1n. To the best of our knowledge, the synthesis of 1e and 1i was reported for the first time.
- Li, Yang,Zhang, Yu,Huang, Zhi,Cao, Xiaoping,Gao, Kun
-
p. 622 - 630
(2007/10/03)
-
- Solvent-free Wittig olefination with stabilized phosphoranes - Scope and limitations
-
Neat mixtures of arene/hetarenecarbaldehydes, alkanals as well as alkenals with alkyl (triphenylphosphoranylidene)acetates react exothermally to furnish the corresponding alkenes. In certain cases, heating has to be provided externally. Reaction times are short and yields are generally very high. Neat mixtures of ketones and alkyl (triphenylphosphoranylidene)acetates react preferentially under microwave irradiation. The better stabilized phosphoranes do not react in the solid state with aldehydes or ketones under conventional heating, but necessitate microwave irradiation, although not all of the phosphoranes have been found to be stable under microwave irradiation at 500 W (2450 MHz).
- Thiemann, Thies,Watanabe, Masataka,Tanaka, Yasuko,Mataka, Shuntaro
-
p. 578 - 584
(2007/10/03)
-
- Synthesis and properties of a stable, cationic, rhodium Lewis-acid catalyst for hydrosilation, Mukaiyama aldol and cyclopropanation reactions
-
The remarkably stable cationic, three-coordinate, 14-electron rhodium complex 1 has been synthesized, isolated and used as a catalyst for hydrosilation, Mukaiyama aldol and cyclopropanation reactions.
- Dias,Brookhart,White
-
p. 423 - 424
(2007/10/03)
-
- Manganese dioxide can oxidise unactivated alcohols under in situ oxidation-Wittig conditions
-
The in situ alcohol oxidation-Wittig reaction using manganese dioxide as the oxidant has been applied to semi-activated and, for the first time, unactivated alcohols to furnish the corresponding α,β-unsaturated esters.
- Blackburn, Leonie,Wei, Xudong,Taylor, Richard J. K.
-
p. 1337 - 1338
(2007/10/03)
-
- Experimental evidence for a [2 + 2] mechanism in the Lewis acid-promoted formation of α,β-unsaturated esters from ethoxyacetylene and aldehydes. Synthesis and characterisation of 4-ethoxyoxetes
-
4-Ethoxy-2H-oxetes 3a-c were prepared from ethoxyacetylene and alkoxy aldehydes 1a-c through MgBr2-Et2O promoted [2 + 2] cycloaddition reaction and were characterized at room temperature; their synthesis, which could occur via the formation of a chelate, establishes cycloaddition as the initial step in the formation of α,β-unsaturated esters 4a-c.
- Oblin, Magali,Parrain, Jean-Luc,Rajzmann, Michel,Pons, Jean-Marc
-
p. 1619 - 1620
(2007/10/03)
-
- Improvement on the synthesis of (E)-alk-3-enoic acids
-
(E)-Alk-3-enoic acids have been prepared in high yield (85-90%) and excellent stereoselectivity (98-99%) by a modified Knoevenagel condensation of a straight carbon chain aldehyde with malonic acid, in dimethyl sulfoxide (DMSO) or dimethylformamide (DMF) at 100°C, in the presence of piperidinium acetate as catalyst. Condensation of the aldehyde with a monoester of malonic acid, under the above conditions, gave the corresponding ester of (E)-alk-3-enoic acid in high yield (76-82%) and good stereoselectivity (90-92%). Condensation of the aldehyde with cyanoacetic acid gave the β,γ-unsaturated nitrile in moderate yield (35-40%) without stereoselectivity.
- Ragoussis, Nikitas,Ragoussis, Valentine
-
p. 3529 - 3533
(2007/10/03)
-
- A synthesis of enantiomerically enriched propargyl silanes
-
Reduction of ethyl 3-methyl-, 3-isopropyl- and 3-n-pentyl-3-[dimethyl(phenyl)silyl]propanoates 4 with DIBAL to the aldehydes 5, enol trifluoromethanesulfonate (triflate) formation using trifluoromethanesulfonic (triflic) anhydride and 2,6-di-tert-butylpyridine, and elimination using LDA, gives the propargyl silanes 8. The esters 4 could also be prepared enantiomerically enriched (11), and the final products are the enantiomerically enriched propargyl (homochiral) silanes 14.
- Fleming, Ian,Mwaniki, Joseph M.
-
p. 1237 - 1247
(2007/10/03)
-
- A new procedure for Horner-Wadsworth-Emmons olefination of carbonyl compounds
-
Aldehydes undergo an efficient E-stereoselective Horner-Wadsworth-Emmons olefination by generation of phosphonate carbanion with lithium hydroxide. The reaction proceeds satisfactorily with linear, cyclic, polifunctional ketones in the presence of activated zeolites and by the slow addition of the base.
- Bonadies, Francesco,Cardilli, Antonella,Lattanzi, Alessandra,Orelli, Liliana R.,Scettri, Arrigo
-
p. 3383 - 3386
(2007/10/02)
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- A chiral synthesis of (-)-cannabisativine: An application of the highly diastereo-selective hetero Diels-Alder reaction
-
The polyamine alkaloid cannabisativine was synthesized as an optical active form. The key step is the hetero Diels-Alder reaction of chiral diene and an N-tosylimine, in which regio- and diastereo-face selectivities were completely controlled, only one diastereomer was isolated in high yield. Synthesized (-)-cannabisativine has the same physical data as the natural product except for the αD value.
- Hamada,Zenkoh,Sato,Yonemitsu
-
p. 1649 - 1652
(2007/10/02)
-
- ORGANIC SYNTHESIS USING HALOBORATION REACTION XV. A NEW SYNTHESIS OF α,β-UNSATURATED ESTERS BY THE HIGHLY CHEMOSELECTIVE REACTION OF B-I-9-BBN-ETHOXYETHYNE ADDUCT WITH ALDEHYDES
-
A haloboration adduct, formed by the reaction of B-iodo-9-borabicyclononanes with ethoxyethyne reacts with aldehydes chemoselectively under very mild conditions.The subsequent hydrolytic work-up affords trans-α,β-unsaturated esters in good yields.
- Satoh, Yoshitaka,Tayano, Takao,Hara, Shoji,Suzuki, Akira
-
p. 5153 - 5156
(2007/10/02)
-
- AN IMPROVED PROCEDURE FOR THE TWO CARBON HOMOLOGATION OF ESTERS TO α,β-UNSATURATED ESTERS
-
Treatment of esters with diisobutylaluminium hydride (DIBAL) in the presence of lithio-trialkylphosphonoacetate results in improved yields of the homologated α,β-unsaturated esters.The problematic overreduction, which has previously observed in the half reduction of esters using DIBAL, is minimal (3percent) under these conditions.
- Takacs, James M.,Helle, Mark A.,Seely, Franklin L.
-
p. 1257 - 1260
(2007/10/02)
-
- Mechanism of Formation of α,β-Unsaturated Esters in the Reaction of Ethyl Mercaptoacetate Dianion with Carbonyl Compounds
-
Dianion derived fron ethyl mercaptoacetate undergoes aldol type reaction with a carbonyl compounds to give an adduct, which exhibited low diastereoselectivity.However, the adducts obtained by the reaction with a variety of aldehydes were subsequently treated with ethyl chloroformate in the presence of trivalent phosphorus compound to give (E)-isomers of α,β-unsaturated esters in high yields with greater than 85percent stereoselectivity regardless of the stereochemistry of the diastereomers of the adducts.The stereochemical mechanism and application of this reaction were studied in detail.
- Matsui, Syuichi
-
p. 426 - 434
(2007/10/02)
-
- A Novel Synthetic Route to (+/-)-Perhydrogephyrotoxin
-
Total synthesis of (+/-)-perhydrogephyrotoxin (3) starting from 1,3-bis(trimethylsiloxy)buta-1,3-diene is presented; an efficient new decarboxylative reduction of γ-carbamoyloxy-α,β-enoate (14) by lithium dibutylcuprate is also presented.
- Ibuka, Toshiro,Chu, G.-Namg,Yoneda, Fumio
-
p. 597 - 599
(2007/10/02)
-
- INFLUENCE OF HETEROAROMATIC AMINES TO KNOEVENANGEL CONDENSATION
-
In the Knoevenagel condensation of hexanal and malonic acid, the ratio of α,β-and β,γ-unsaturated acids was remarkably affected by the nature of tertiary amines used as a catalyst.That is, the condensation in pyridine or isoquinoline gave 2-octenoic acid selectively, whereas the condensation in 2-methylpyridine, 2,6-dimethylpyridine, or quinoline gave 3-octenoic acid as the main product.
- Yamanaka, Hiroshi,Yokoyama, Masaaki,Sakamoto, Takao,Shiraishi, Takayuki,Sagi, Mataichi,Mizugaki, Michinao
-
p. 1541 - 1544
(2007/10/02)
-
- Stereoselective Synthesis of α,β-Unsaturated Esters
-
Reaction of α-silylated ester magnesium enolates with aldehydes affords exclusively one diastereoisomer of the two possible β-hydroxy silanes which give pure E-unsaturated esters on acid work-up.
- Larcheveque, Marc,Debal, Alain
-
p. 877 - 878
(2007/10/02)
-