Literature DB >> 29232022

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

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

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.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

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

Year:  2018        PMID： 29232022     DOI： 10.1002/anie.201712088

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  12 in total

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4.  An Experimental Acidity Scale for Intramolecularly Stabilized Silyl Lewis Acids.

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6.  Confinement-Controlled, Either syn- or anti-Selective Catalytic Asymmetric Mukaiyama Aldolizations of Propionaldehyde Enolsilanes.

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Journal:  J Am Chem Soc       Date:  2021-08-26       Impact factor: 15.419

7.  Design of an Organocatalytic Asymmetric (4 + 3) Cycloaddition of 2-Indolylalcohols with Dienolsilanes.

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Journal:  Org Lett       Date:  2022-01-20       Impact factor: 6.005

10.  Isothiourea-catalysed enantioselective Michael addition of N-heterocyclic pronucleophiles to α,β-unsaturated aryl esters.

Authors:  Chang Shu; Honglei Liu; Alexandra M Z Slawin; Cameron Carpenter-Warren; Andrew D Smith
Journal:  Chem Sci       Date:  2019-10-23       Impact factor: 9.825
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