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Practical Method for Asymmetric Addition of Arylboronic Acids to α,β-Unsaturated Carbonyl Compounds Utilizing an In Situ Prepared Rhodium Catalyst

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Kirill Lukin*, Qunying Zhang and M. Robert Leanna

GPRD Process Research and Development, Abbott Laboratories, North Chicago, Illinois 60064

J. Org. Chem., 2009, 74 (2), pp 929–931

DOI: 10.1021/jo802136j

Publication Date (Web): December 5, 2008

Abstract

A new practical method for the asymmetric Michael addition of arylboronic acids to α,β-unsaturated carbonyl compounds utilizing in situ generated chiral rhodium-binap-based catalyst has been developed to address the unavailability of the preformed catalysts. While maintaining high levels of enantioselectivity reported for the preformed catalysts, the new method provides a convenient access to either enantiomeric form of the product and allows for a substantial reductions in both the boronic acid and the catalyst loads.

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Published In Issue January 16, 2009
Article ASAPDecember 05, 2008
Received: September 24, 2008

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Practical Method for Asymmetric Addition of Arylboronic Acids to α,β-Unsaturated Carbonyl Compounds Utilizing an In Situ Prepared Rhodium Catalyst