Rhodium-catalyzed enantioselective conjugate addition of organoboronic acids to alpha,beta-unsaturated sulfones

Organic Letters
Pablo Mauleón, Juan C Carretero

Abstract

[reaction: see text] A general method for the enantioselective catalytic conjugate addition to acyclic alpha,beta-unsaturated sulfones is described. Using metal-chelating alpha,beta-unsaturated pyridyl sulfones as substrates, the rhodium-catalyzed chiraphos-mediated addition of organoboric acids takes place in excellent yield and high enantioselectivity. The subsequent elimination of the pyridylsulfonyl group by Julia-Kociensky olefination provides a novel approach to the enantioselective synthesis of allylic substituted alkenes.

Citations

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May 27, 2006·Organic & Biomolecular Chemistry·Tian-Yu LiuYing-Chun Chen
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