- Synthesis and olfactory evaluation of (4afl*,8afl*)-1,1,8a- trimethyl- Decahydronaphthalen-4a-ol: A cis -decalol intersection structure of (-)-patchoulol and (5fl*,6S*)-1,1,6-trimethylspiro[4.5]decan-6-ol
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Superposition analysis of (-)-patchoulol (1) and the spi- rocyclic patchouli odorant (5R*,6S*)-1,1,6-trmiethylspiro[4.5]de- can-6-ol (3) suggested the intersection structure (4a5*,8a5*)- 1,1,8a-trimethyldecahydronaphthalen-4a-ol (4) as potential patchouli
- Jahnke, Astrid,Burschka, Christian,Tacke, Reinhold,Kraft, Philip
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Read Online
- Generation and trapping of electron-deficient 1,2-cyclohexadienes. Unexpected hetero-Diels-Alder reactivity
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Keto-substituted 1,2-cyclohexadienes were generated by base-mediated (KOt-Bu) elimination, and found to dimerize via an unprecedented formal hetero-Diels-Alder process, followed by hydration. These highly reactive cyclic allene intermediates were also tra
- Wang, Baolei,Constantin, Marius-Georgian,Singh, Simarpreet,Zhou, Yuqiao,Davis, Rebecca L.,West
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p. 399 - 405
(2021/01/29)
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- 5-(Cyano)dibenzothiophenium Triflate: A Sulfur-Based Reagent for Electrophilic Cyanation and Cyanocyclizations
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The synthesis of 5-(cyano)dibenzothiophenium triflate 9, prepared by activation of dibenzo[b,d]thiophene-5-oxide with Tf2O and subsequent reaction with TMSCN is reported, and its reactivity as electrophilic cyanation reagent evaluated. The scalable preparation, easy handling and broad substrate scope of the electrophilic cyanation promoted by 9, which includes amines, thiols, silyl enol ethers, alkenes, electron rich (hetero)arenes and polyaromatic hydrocarbons, illustrate the synthetic potential of this reagent. Importantly, Lewis acid activation of the reagent is not required for the transfer process. We additionally report herein biomimetic cyanocyclization cascade reactions, which are not promoted by typical electrophilic cyanation reagents, demonstrating the superior ability of 9 to trigger challenging transformations.
- Li, Xiangdong,Golz, Christopher,Alcarazo, Manuel
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supporting information
p. 9496 - 9500
(2019/06/27)
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- SUBSTITUTED IMIDAZOLIUM SULFURANES AND THEIR USE
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The present invention refers to substituted imidazolium sulfuranes, the use thereof for the transfer of a -CN group or an alkyne group.
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Page/Page column 15; 17
(2017/01/26)
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- Dihalo(imidazolium)sulfuranes: A Versatile Platform for the Synthesis of New Electrophilic Group-Transfer Reagents
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The syntheses of imidazolium thiocyanates and imidazolium thioalkynes from dihalo(imidazolium) sulfuranes are reported and their reactivities as CN+ and R-CC+ synthons evaluated, respectively. The easy and scalable preparation of these electrophilic reagents, their operationally simple handling, broad substrate scope, and functional group tolerance clearly illustrate the potential of these species to become a reference for the direct electrophilic cyanation and alkynylation of organic substrates.
- Talavera, Garazi,Pe?a, Javier,Alcarazo, Manuel
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supporting information
p. 8704 - 8707
(2015/07/27)
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- Cytochrome P450 catalyzed oxidative hydroxylation of achiral organic compounds with simultaneous creation of two chirality centers in a single C-H activation step
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Regio- and stereoselective oxidative hydroxylation of achiral or chiral organic compounds mediated by synthetic reagents, catalysts, or enzymes generally leads to the formation of one new chiral center that appears in the respective enantiomeric or diastereomeric alcohols. By contrast, when subjecting appropriate achiral compounds to this type of C-H activation, the simultaneous creation of two chiral centers with a defined relative and absolute configuration may result, provided that control of the regio-, diastereo-, and enantioselectivity is ensured. The present study demonstrates that such control is possible by using wild type or mutant forms of the monooxygenase cytochrome P450 BM3 as catalysts in the oxidative hydroxylation of methylcyclohexane and seven other monosubstituted cyclohexane derivatives.
- Roiban, Gheorghe-Doru,Agudo, Ruben,Reetz, Manfred T.
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supporting information
p. 8659 - 8663
(2014/08/18)
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- An Alternative to the Classical α-Arylation: The Transfer of an Intact 2-Iodoaryl from ArI(O2CCF3)2
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The α-arylation of carbonyl compounds is generally accomplished under basic conditions, both under metal catalysis and via aryl transfer from the diaryl λ3-iodanes. Here, we describe an alternative metal-free α-arylation using ArI(O2CCF3)2 as the source of a 2-iodoaryl group. The reaction is applicable to activated ketones, such as α-cyanoketones, and works with substituted aryliodanes. This formal C-H functionalization reaction is thought to proceed through a [3,3] rearrangement of an iodonium enolate. The final α-(2-iodoaryl)ketones are versatile synthetic building blocks.
- Jia, Zhiyu,Gálvez, Erik,Sebastián, Rosa María,Pleixats, Roser,álvarez-Larena, ángel,Martin, Eddy,Vallribera, Adelina,Shafir, Alexandr
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p. 11298 - 11301
(2016/02/19)
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- A new and facile synthesis of methyl 3-amino-4,5,6,7-tetrahydrobenzo[b] thiophene-2-carboxylate
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A four-step synthesis of methyl 3-amino-4,5,6,7-tetrahydrobenzo[b] thiophene-2-carboxylate from commercially available starting materials is presented.
- Tenora, Luká?,Buchlovi?, Marian,Man, Stanislav,Potá?ek, Milan
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supporting information; experimental part
p. 401 - 403
(2011/02/28)
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- An approach to azabicyclo[ n.3.1]alkanes by double mannich reaction
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Chlorotrimethylsilane-promoted double Mannich annulation of ketones using N,N-bis(methoxymethyl)benzylamine has been explored. It has been shown that the structure of the substrate drastically influenced the outcome of the reaction. The method allows azabicyclo[n.3.1]alkane derivatives (n=2-5) to be obtained in good yields. Georg Thieme Verlag Stuttgart New York.
- Mityuk, Andrey P.,Denisenko, Aleksandr V.,Dacenko, Oleksandr P.,Grygorenko, Oleksandr O.,Mykhailiuk, Pavel K.,Volochnyuk, Dmitriy M.,Shishkin, Oleg V.,Tolmachev, Andrey A.
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experimental part
p. 493 - 497
(2010/04/26)
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- A modified Robinson annulation process to α,α-disubstituted-β,γ-unsaturated cyclohexanone system. Application to the total synthesis of nanaimoal
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4-Cyano-2-cyclohexenones were found to be susceptible to reductive alkylation reactions, giving the corresponding 2,2-disubstituted-3-cyclohexenone derivatives in a completely regioselective manner. This newly developed methodology has been successfully applied towards the total synthesis, in racemic form, of the marine natural product nanaimoal.
- Liu, Hsing-Jang,Ly, Tai Wei,Tai, Chia-Liang,Wu, Jen-Dar,Liang, Jinn-Kwei,Guo, Jiunn-Cheh,Tseng, Nai-Wen,Shia, Kak-Shan
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p. 1209 - 1226
(2007/10/03)
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- Preparation of enantiopure ketones and alcohols containing a quaternary stereocenter through parallel kinetic resolution of β-keto nitriles
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Racemic 1-methyl-2-oxocycloalkanecarbonitriles have been subjected to bioreduction by the fungus Mortierella isabellina NRRL 1757 through a parallel kineticresolution process. The u and l alcohols thus obtained (up to >99% ee) were easily separated and oxidized to the R and S ketones, respectively. The process can be then repeated so that both enantiomers of the ketone and two epimers of the alcohol can be obtained in their enantiopure forms.
- Dehli, Juan R.,Gotor, Vicente
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p. 1716 - 1718
(2007/10/03)
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- Dynamic kinetic resolution of 2-oxocycloalkanecarbonitriles: Chemoenzymatic syntheses of optically active cyclic β- and γ-amino alcohols
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A series of fungi and yeasts have been tested for the stereoselective bioreduction of 2-oxocycloalkanecar-bonitriles, 1. The yeast Saccharomyces montanus CBS 6772 yielded the corresponding cis-hydroxy nitriles, 2, in >90% ee and de and in high chemical yields. Through simple and efficient procedures, they were transformed into optically active 2-amino and 2-aminomethyl cycloalkanols.
- Dehli, Juan R.,Gotor, Vicente
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p. 6816 - 6819
(2007/10/03)
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- Polycyclic compounds
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PCT No. PCT/GB96/02945 Sec. 371 Date Aug. 25, 1998 Sec. 102(e) Date Aug. 25, 1998 PCT Filed Nov. 28, 1996 PCT Pub. No. WO97/19929 PCT Pub. Date Jun. 5, 1997Compounds of Formula (I), methods for their preparation, pharmaceutical formulations and use thereof.
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- The synthesis of pyrido[3,2-a]acridines
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6-Aminoquinoline (5) reacts with 2-cyanocyclohexanone (6a) or ethyl 2-oxocyclohexanecarboxylate (6b) to give enamines which can be cyclised, under Lewis acid catalysed conditions, to tetrahydropyrido[3,2-a]acridines (9, 13). Dehydrogenation of these tetra
- Groundwater, Paul W.,Munawar, Munawar Ali
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p. 2463 - 2469
(2007/10/03)
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- A convenient and improved procedure for the cyanation of enamines and 1,3-dicarboxyl compounds
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The direct cyanation of enamines 2a-f using acylsubstituted cyanatobenzenes 1a-c and cyanatoanthraquinone 1d furnishes β-cyanoenamines 3a-f which upon hydrolysis afford the cyanoketones 4a,b. 2-Cyano-1,3-diketones 6a-c are obtained starting from compounds
- Buttke,Niclas
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p. 3241 - 3248
(2007/10/02)
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- ULTRASOUND IN ORGANIC SYNTHESIS 5. PREPARATION AND SOME REACTIONS OF COLLOIDAL POTASSIUM
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colloidal potassium is easily obtained by ultrasonic irradiation in toluene.Some of its reactions with organic substrates are given.
- Luche, J.L.,Petrier, C.,Dupuy, C.
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p. 753 - 756
(2007/10/02)
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- Ion Radicals. 46. Reactions of the Adducts of Thianthrene and Phenoxathiin Cation Radicals and Cyclohexene with Nucleophiles
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Thianthrene cation radical perchlorate 1a reacts with cyclohexene to give an adduct .Reactions of 2a with CN-, C6H5S-, and I- have been studied in dimethyl sulfoxide (Me2SO) and ethanol at room temperature.Reaction of the analogous adduct of cyclohexene and phenoxathiin cation radical perchlorate 2b with I- in ethanol was also studied.The reactions indicate that the adducts have the trans-1,2 structure and undergo facile substitution (SN2) and subsequent elimination (E2) reactions at room temperature.
- Iwai, Kiyoshi,Shine, Henry J.
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p. 271 - 276
(2007/10/02)
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