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. 2018 Feb 23;57(9):2464-2468.
doi: 10.1002/anie.201712088. Epub 2018 Jan 26.

The Catalytic Asymmetric Mukaiyama-Michael Reaction of Silyl Ketene Acetals with α,β-Unsaturated Methyl Esters

Tim Gatzenmeier  1 , Philip S J Kaib  1 , Julia B Lingnau  1 , Richard Goddard  1 , Benjamin List  1
Affiliations

The Catalytic Asymmetric Mukaiyama-Michael Reaction of Silyl Ketene Acetals with α,β-Unsaturated Methyl Esters

Tim Gatzenmeier et al. Angew Chem Int Ed Engl. .

Abstract

α,β-Unsaturated esters are readily available but challenging substrates to activate in asymmetric catalysis. We now describe an efficient, general, and highly enantioselective Mukaiyama-Michael reaction of silyl ketene acetals with α,β-unsaturated methyl esters that is catalyzed by a silylium imidodiphosphorimidate (IDPi) Lewis acid.

Keywords: Brønsted acids; Mukaiyama-Michael reaction; cinnamates; organocatalysis; silyl ketene acetals.

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