American Chemical Society
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Antibody-Catalyzed Asymmetric Intramolecular Michael Addition of Aldehydes and Ketones to Yield the Disfavored Cis-Product

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journal contribution
posted on 2005-09-28, 00:00 authored by Roy Weinstain, Richard A. Lerner, Carlos F. Barbas, Doron Shabat
The development of new catalytic asymmetric reactions continues to be a major goal in organic chemistry. Here we report a novel antibody-catalyzed intramolecular Michael addition of aldehydes and ketones to enones. The reaction is enantioselective and diastereoselective with a high ee value and cis/trans ratio. This is the first example of asymmetric intramolecular Michael addition of ketones. Antibody 38C2 is the only catalyst to date capable of generating this selectivity in Michael addition products.