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

Tim Gatzenmeier; Philip S J Kaib; Julia B Lingnau; Richard Goddard; Benjamin List

doi:10.1002/anie.201712088

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

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

Authors

Tim Gatzenmeier¹, Philip S J Kaib¹, Julia B Lingnau¹, Richard Goddard¹, Benjamin List¹

Affiliation

¹ Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470, Mülheim an der Ruhr, Germany.

PMID: 29232022
DOI: 10.1002/anie.201712088

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.

Publication types

Research Support, Non-U.S. Gov't