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Mini-Reviews in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-193X
ISSN (Online): 1875-6298

Asymmetric Baylis-Hillman Reaction: Use of Novel Chiral Aldehydes as Electrophiles, Chiral Base Catalysts and Auxilliaries&#

Author(s): Palakodety R. Krishna and G. V.M. Sharma

Volume 3, Issue 2, 2006

Page: [137 - 153] Pages: 17

DOI: 10.2174/157019306776819253

Price: $65

Abstract

The present review highlights our recent research findings in the field of asymmetric Baylis-Hillman reaction. In particular, it elaborates on the following efficient aids: 1) utilization of sugar-derived acrylates as chiral auxiliary for diastereoselective Baylis-Hillman reaction; 2) use of novel chiral electrophiles such as sugar-derived aldehydes and chiral 2,3-epoxy aldehydes for the diastereoselective Baylis-Hillman reaction to obtain valuable chiral adducts; 3) a novel prolinol derivative promoted enantioselective Baylis-Hillman reaction and 4) intramolecular Baylis-Hillman reaction wherein both the aldehyde and acrylate component are part structure of the same molecular framework to afford high des. This review also covers the related research work from other groups on asymmetric Baylis-Hillman reaction.

Keywords: Sugar-derived acrylate, sugar-derived aldehydes, chiral 2,3-epoxy aldehydes, Double Asymmetric Induction, Nmethylprolinol, intramolecular Baylis-Hillman reaction


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