Asymmetric Synthesis of 3,3-diarylpropanals with Chiral Diene-rhodium Catalysts

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2005 Aug 4

PMID 16076189

Citations 15

Authors

Jean-Francois Paquin

Christian Defieber

Corey R J Stephenson

Erick M Carreira

Affiliations

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Abstract

A general route to enantioenriched 3,3-diarylpropanals is presented. These useful building blocks are prepared via an asymmetric rhodium-catalyzed conjugate addition of arylboronic acids to cinnamaldehyde derivatives in the presence of chiral dienes. The addition of both electron-poor as well as electron-rich boronic acids proceeds smoothly with various enals in 63-90% yield with high enantioselectivities (89-93% ee).

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