Issue 78, 2019
From the journal:

Chemical Communications

Trapping of chiral enolates generated by Lewis acid promoted conjugate addition of Grignard reagents to unreactive Michael acceptors by various electrophiles†

Denisa Vargová, ORCID logo ab   Juana M. Pérez, ORCID logo b   Syuzanna R. Harutyunyanb  and  Radovan Šebesta ORCID logo *a  

* Corresponding authors

a Comenius University in Bratislava, Faculty of Natural Sciences, Department of Organic Chemistry, Mlynska dolina, Ilkovičova 6, 84215 Bratislava, Slovakia
E-mail: radovan.sebesta@uniba.sk

b Stratingh Institute for Chemistry, Rijksuniversiteit Groningen, Nijenborgh 4, Groningen, The Netherlands

Abstract

Here we show trapping of chiral enolates with carbenium ions, Michael acceptors, and bromine. Silyl ketene aminals, disilyl acetals, and aza-enolates were obtained via Lewis acid mediated enantioselective conjugate addition of Grignard reagents to unsaturated amides, carboxylic acids and alkenyl heterocycles.

Graphical abstract: Trapping of chiral enolates generated by Lewis acid promoted conjugate addition of Grignard reagents to unreactive Michael acceptors by various electrophiles

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Article information

DOI
https://doi.org/10.1039/C9CC05041H
Article type
Communication
Submitted
02 Jul 2019
Accepted
05 Sep 2019
First published
05 Sep 2019

Chem. Commun., 2019,55, 11766-11769

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Trapping of chiral enolates generated by Lewis acid promoted conjugate addition of Grignard reagents to unreactive Michael acceptors by various electrophiles

D. Vargová, J. M. Pérez, S. R. Harutyunyan and R. Šebesta, Chem. Commun., 2019, 55, 11766 DOI: 10.1039/C9CC05041H

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