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Selective Synthesis of α,β-Unsaturated Ketones by Dibutyltin Dimethoxide-Catalyzed Condensation of Aldehydes with Alkenyl Trichloroacetates
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Abstract
Various α,β-unsaturated ketones were stereoselectively synthesized in high yields up to 94% by a condensation reaction between alkenyl trichloroacetates and aldehydes using dibutyltin dimethoxide as a catalyst in the presence of methanol. This process is superior to the classical Claisen−Schmidt condensation with respect to mildness of the base catalyst and product selectivity.
Citing Articles
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This article has been cited by 5 ACS Journal articles (5 most recent appear below).
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Thermal and Metal-Catalyzed Cyclization of 1-Substituted 3,5-Dien-1-ynes via a [1,7]-Hydrogen Shift: Development of a Tandem Aldol Condensation−Dehydration and Aromatization Catalysis between 3-En-1-yn-5-al Units and Cyclic Ketones
Jian-Jou Lian, Chung-Chang Lin, Hsu-Kai Chang, Po-Chiang Chen, and Rai-Shung LiuJournal of the American Chemical Society2006 128 (30), 9661-9667Thermal and Metal-Catalyzed Cyclization of 1-Substituted 3,5-Dien-1-ynes via a [1,7]-Hydrogen Shift: Development of a Tandem Aldol Condensation−Dehydration and Aromatization Catalysis between 3-En-1-yn-5-al Units and Cyclic Ketones
Jian-Jou Lian, Chung-Chang Lin, Hsu-Kai Chang, Po-Chiang Chen, and Rai-Shung LiuJournal of the American Chemical Society2006 128 (30), 9661-9667This work investigates the feasibility of thermal and catalytic cyclization of 6,6-disubstituted 3,5-dien-1-ynes via a 1,7-hydrogen shift. Our strategy began with an understanding of a structural correlation of 3,5-dien-1-ynes with their thermal ...
A Novel Pyrrolidine Imide Catalyzed Direct Formation of α,β-Unsaturated Ketones from Unmodified Ketones and Aldehydes
Wei Wang, Yujiang Mei, Hao Li, and Jian WangOrganic Letters2005 7 (4), 601-604A Novel Pyrrolidine Imide Catalyzed Direct Formation of α,β-Unsaturated Ketones from Unmodified Ketones and Aldehydes
Wei Wang, Yujiang Mei, Hao Li, and Jian WangOrganic Letters2005 7 (4), 601-604A method for direct, stereoselective preparation of (E)-α,β-unsaturated ketones from ketones and aldehydes, promoted by a novel pyrrolidine imide organocatalyst, has been developed in moderate to high yields. Unlike the Claisen−Schmidt condensation and ...
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History
- Published In Issue November 11, 2004
- Received August 29, 2004
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