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Highly Enantioselective Phenylacetylene Additions to Both Aliphatic and Aromatic Aldehydes
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Abstract
The readily available and inexpensive BINOL in combination with Ti(OiPr)4 is found to catalyze the reaction of an alkynylzinc reagent with various types of aldehydes including aliphatic aldehydes, aromatic aldehydes, and other α,β-unsaturated aldehydes to generate chiral propargyl alcohols with 91−99% ee at room temperature. No previous chiral catalysts have exhibited such a broad scope of enantioselectivity with respect to the type of aldehydes for this reaction.
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This article has been cited by 42 ACS Journal articles (5 most recent appear below).
From Highly Enantioselective Catalytic Reaction of 1,3-Diynes with Aldehydes to Facile Asymmetric Synthesis of Polycyclic Compounds
Mark Turlington, Yuhao Du, Samuel G. Ostrum, Vishaka Santosh, Kathryne Wren, Tony Lin, Michal Sabat, and Lin PuJournal of the American Chemical Society2011 Article ASAPFrom Highly Enantioselective Catalytic Reaction of 1,3-Diynes with Aldehydes to Facile Asymmetric Synthesis of Polycyclic Compounds
Mark Turlington, Yuhao Du, Samuel G. Ostrum, Vishaka Santosh, Kathryne Wren, Tony Lin, Michal Sabat, and Lin PuJournal of the American Chemical Society2011 Article ASAP(S)-1,1′-Binaphth-2-ol (BINOL) in combination with ZnEt2, Ti(OiPr)4, and biscyclohexylamine was found to catalyze the highly enantioselective (83–95% ee) addition of various 1,3-diynes to aldehydes of diverse structures. This method provides a convenient ...
Tetrabutylammonium Fluoride (TBAF)-Catalyzed Addition of Substituted Trialkylsilylalkynes to Aldehydes, Ketones, and Trifluoromethyl Ketones
Venkat Reddy Chintareddy, Kuldeep Wadhwa, and John G. VerkadeThe Journal of Organic Chemistry2011 Article ASAPTetrabutylammonium Fluoride (TBAF)-Catalyzed Addition of Substituted Trialkylsilylalkynes to Aldehydes, Ketones, and Trifluoromethyl Ketones
Venkat Reddy Chintareddy, Kuldeep Wadhwa, and John G. VerkadeThe Journal of Organic Chemistry2011 Article ASAPHerein we report that tetrabutylammonium fluoride (TBAF) is a very efficient catalyst for the addition of trialkylsilylalkynes to aldehydes, ketones, and trifluoromethyl ketones in THF solvent at room temperature. The reaction conditions are mild and ...
Enantioselective Total Synthesis of (+)-Lysergic Acid, (+)-Lysergol, and (+)-Isolysergol by Palladium-Catalyzed Domino Cyclization of Allenes Bearing Amino and Bromoindolyl Groups
Shinsuke Inuki, Akira Iwata, Shinya Oishi, Nobutaka Fujii, and Hiroaki OhnoThe Journal of Organic Chemistry2011 76 (7), 2072-2083Enantioselective Total Synthesis of (+)-Lysergic Acid, (+)-Lysergol, and (+)-Isolysergol by Palladium-Catalyzed Domino Cyclization of Allenes Bearing Amino and Bromoindolyl Groups
Shinsuke Inuki, Akira Iwata, Shinya Oishi, Nobutaka Fujii, and Hiroaki OhnoThe Journal of Organic Chemistry2011 76 (7), 2072-2083Enantioselective total synthesis of the biologically important indole alkaloids (+)-lysergol, (+)-isolysergol, and (+)-lysergic acid is described. Key features of these total synthesis include (1) a facile synthesis of a chiral 1,3-amino alcohol via the ...
Enantioselective Alkynylation of Aldehydes with 1-Haloalkynes Catalyzed by Tethered Bis(8-quinolinato) Chromium Complex
Dmitry L. Usanov and Hisashi YamamotoJournal of the American Chemical Society2011 133 (5), 1286-1289Enantioselective Alkynylation of Aldehydes with 1-Haloalkynes Catalyzed by Tethered Bis(8-quinolinato) Chromium Complex
Dmitry L. Usanov and Hisashi YamamotoJournal of the American Chemical Society2011 133 (5), 1286-1289The first example of Cr-catalyzed asymmetric alkynylation of aldehydes with 1-iodo- and 1-bromoalkynes was developed. The use of tethered bis(8-quinolinato) chromium catalyst (3 mol %) allowed preparation of enantioenriched propargyl alcohols with good ...
Catalytic Asymmetric Synthesis of Chiral Propargylic Alcohols for the Intramolecular Pauson−Khand Cycloaddition
Mark Turlington, Yang Yue, Xiao-Qi Yu, and Lin PuThe Journal of Organic Chemistry2010 75 (20), 6941-6952Catalytic Asymmetric Synthesis of Chiral Propargylic Alcohols for the Intramolecular Pauson−Khand Cycloaddition
Mark Turlington, Yang Yue, Xiao-Qi Yu, and Lin PuThe Journal of Organic Chemistry2010 75 (20), 6941-6952Several methods for the catalytic asymmetric alkyne addition to aldehydes are used to prepare the propargylic alcohol-based chiral en-ynes. Protection of the propargylic alcohols with either an acetyl or a methyl group allows the resulting en-ynes to ...
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History
- Published In Issue November 14, 2002
- Received September 17, 2002
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