- One-Pot γ-Lactonization of Homopropargyl Alcohols via Intramolecular Ketene Trapping
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A one-pot γ-lactonization of homopropargyl alcohols via an alkyne deprotonation/boronation/oxidation sequence has been developed. Oxidation of the generated alkynyl boronate affords the corresponding ketene intermediate, which is trapped by the adjacent hydroxy group to furnish the γ-lactone. We have optimized the conditions as well as examined the substrate scope and synthetic applications of this efficient one-pot lactonization.
- Yamane, Daichi,Tanaka, Haruna,Hirata, Akihiro,Tamura, Yumiko,Takahashi, Daichi,Takahashi, Yusuke,Nagamitsu, Tohru,Ohtawa, Masaki
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supporting information
p. 2831 - 2835
(2021/05/05)
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- Regioselective access to CF3S-substituted dihydrofurans from homopropargylic alcohols with trifluoromethanesulfenamide
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A facile access to 4-((trifluoromethyl)thio)-2,3-dihydrofurans from unprotected homopropargylic alcohols in high regioselectivity is reported. This method is the first example of using a free hydroxy group as a nucleophile to complete a trifluoromethylthiolation/cyclization protocol with an alkyne in moderate to excellent yields. This journal is
- Chen, Dao-Qian,Gao, Pin,Zhou, Ping-Xin,Song, Xian-Rong,Qiu, Yi-Feng,Liu, Xue-Yuan,Liang, Yong-Min
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supporting information
p. 6637 - 6639
(2015/04/14)
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- Efficient synthesis of γ-lactones via gold-catalyzed tandem cycloisomerization/oxidation
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A novel Au-catalyzed tandem cycloisomerization/oxidation of homopropargyl alcohols was developed. Various γ-lactones can be accessed readily by utilizing this strategy. Notably, the mechanism of this reaction is distinctively different from the related Ru-catalyzed reactions where the ruthenium vinylidene intermediate was proposed.
- Shu, Chao,Liu, Meng-Qi,Sun, Yu-Zhe,Ye, Long-Wu
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supporting information
p. 4958 - 4961,4
(2012/12/12)
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- Efficient synthesis of γ-lactones via gold-catalyzed tandem cycloisomerization/oxidation
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A novel Au-catalyzed tandem cycloisomerization/oxidation of homopropargyl alcohols was developed. Various γ-lactones can be accessed readily by utilizing this strategy. Notably, the mechanism of this reaction is distinctively different from the related Ru-catalyzed reactions where the ruthenium vinylidene intermediate was proposed.
- Shu, Chao,Liu, Meng-Qi,Sun, Yu-Zhe,Ye, Long-Wu
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supporting information
p. 4958 - 4961
(2013/01/15)
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- A new synthesis of γ-butyrolactones via AuCl3- or Hg(II)-catalyzed intramolecular hydroalkoxylation of 4-bromo-3-yn-1-ols
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An efficient conversion of 4-bromo-3-yn-1-ols to γ-butyrolactones via AuCl3-catalyzed electrophilic cyclization (hydroxyl-assisted regioselective hydration) in wet toluene is described. Various secondary and tertiary alcohols including benzylic systems were found to be equally reactive with moderate to excellent yields obtained in all cases.
- Reddy, Maddi Sridhar,Kumar, Yalla Kiran,Thirupathi, Nuligonda
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scheme or table
p. 824 - 827
(2012/04/05)
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- Preparation of 5-membered rings via radical addition-translocation- cyclization (RATC) processes mediated by diethyl thiophosphites
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A practical method for the formation of thiophosphonates bearing functionalized monocyclic, fused bicyclic and spirocyclic residues is presented. The procedure requires the easily available terminal alkynes as starting materials as well as commercially an
- Lamarque, Christophe,Beaufils, Florent,Denes, Fabrice,Schenk, Kurt,Renaud, Philippe
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supporting information; experimental part
p. 1353 - 1358
(2011/06/26)
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- INHIBITORS OF DIACYLGLYCEROL O-ACYLTRANSFERASE TYPE 1 ENZYME
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The present invention relates to compounds of formula (I): wherein R1, R2, and R3, are defined herein. Pharmaceutical compositions and methods for treating DGAT-1 related diseases or conditions are also disclosed.
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Page/Page column 65
(2008/12/08)
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- Preparation of homoallylic homopropargylic alcohols from 2-vinyloxiranes
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(Chemical Equation Presented) β,γ-Unsaturated aldehydes generated in situ by treatment of 2-vinyloxiranes with a catalytic amount of Sc(OTf)3 or BF·OEt2 are effectively trapped by B-allenyl-9-BBN to afford homoallylic homopropargylic alcohols in high yield. An enantioselective version has been demonstrated, and a convenient synthesis of 9-allenyl-9-BBN is described.
- Maddess, Matthew L.,Lautens, Mark
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p. 3557 - 3560
(2007/10/03)
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- A new method for the preparation of 1,3-dilithiopropyne: An efficient synthesis of homopropargyl alcohols
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Controlled dilithiation of propargyl bromide with two equivalents of n-butyllithium, in the presence of TMEDA, produces the operational equivalent of the dianion 1,3-dilithiopropyne. The latter reacts efficiently with aldehydes and ketones to produce homo
- Cabezas, Jorge A,Pereira, Albán R,Amey, Adam
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p. 6819 - 6822
(2007/10/03)
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- Propargylation of carbonyl compounds: An efficient method for the synthesis of homopropargyl alcohols
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Controlled dilithiation of allene, with two equivalents of n- butyllithium, produces the propargyl dianion 5. The latter couples efficiently with carbonyl compounds to produce homopropargyl alcohol in high yields.
- Cabezas, Jorge A.,Alvarez, Leonardo X.
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p. 3935 - 3938
(2007/10/03)
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- Organoboranes for Synthesis. 15. B-Allenyl-9-BBN: A Highly Regiospecific and Chemoselective Reagent for Allenylboration of Representative Carbonyl Compounds, Leading to Homopropargylic Alcohols and Amines
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Reactions of B-allenyl-9-BBN (11) with representative carbonyl compounds, such as aldehydes, ketones, acid chlorides, carboxylic acid esters, and imines, proceed cleanly with the allenyl moiety undergoing transfer to the carbonyl or imine carbon, with allenic to propargylic rearrangement, and the boron moiety to the carbonyl oxygen or imine nitrogen.A simple oxidation with alkaline hydrogen peroxide results in the formation of the corresponding homopropargylic alcohols and amines in excellent yields.Aldehydes, ketones, and imines react in a 1:1 stoichiometry, while acid chlorides and carboxylic acid esters react with 2 equiv of the reagent.The relative reactivities of representative aldehydes, ketones, and esters toward 11 were also explored.Besides being highly regiospecific, the reagent 11 also possesses a remarkable chemoselectivity.B-Allenyl-9-BBN can distinguish between less and more sterically hindered aldehydes, ketones, and esters, making possible the clean and selective propargylboration of a desired carbonyl group in complex organic molecules containing less reactive functional groups.
- Brown, Herbert C.,Khire, Uday R.,Narla, Gowriswari,Racherla, Uday S.
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p. 544 - 549
(2007/10/02)
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- 9-Allenyl-9-BBN: A new reagent for the efficient allenylboration of carbonyl compounds producing the homopropargylic alcohols in high purity and yield
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A new reagent, 9-allenyl-9-BBN (1), has been developed for the convenient and efficient synthesis of a variety of homopropargylic alcohols.
- Brown, Herbert C.,Khire, Uday R.,Racherla, Uday S.
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