Synlett
DOI: 10.1055/s-0041-1737323
synpacts

Stereoselective Michael Additions of Arylacetic Acid Derivatives by Asymmetric Organocatalysis

Byungjun Kim
,
Yongjae Kim
,
This work was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT & Future Planning (2021R1A2C4001752).


Abstract

Because of the versatility of chiral 1,5-dicarbonyl structural motifs, the development of stereoselective Michael additions of arylacetic acid derivatives to electron-deficient alkenes is an important challenge. Over recent decades, an array of enantio- and diastereoselective methods of this type have been developed through the use of chiral organocatalysts. In this article, three distinct strategies in this research area are highlighted. Catalytic generation of either a chiral iminium electrophile (iminium catalysis) or a chiral enolate nucleophile (Lewis­ base catalysis) has allowed the efficient construction of stereogenic C–C bonds. We also introduce a synergistic catalytic approach involving the merger of these two catalytic cycles that provides selective access to all four stereoisomers of products with vicinal stereocenters.

1 Introduction

2 Iminium Catalysis

3 Lewis Base Catalysis

4 Synergistic Organocatalysis

5 Summary



Publication History

Received: 11 November 2021

Accepted after revision: 29 November 2021

Publication Date:
05 January 2022 (online)

© 2022. Thieme. All rights reserved

Georg Thieme Verlag KG
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