Recent Advances in Asymmetric [1,2]-Stevens-Type Rearrangement via Metal Carbenes

Abstract

The [1,2]-Stevens rearrangement is a widely used transformation in synthetic organic chemistry. However, enantioselective versions are relatively limited and most of them rely on substrate-induced methodologies. In recent years, metal carbene chemistry has been extensively investigated, and the related asymmetric [1,2]-Stevens rearrangement has experienced rapid development by employing ylide intermediates generated from the reaction of metal carbenes with heteroatoms. This review summarizes recent advances in the asymmetric [1,2]-Stevens-type rearrangement via metal carbenes by presenting their product diversity, selectivity, and mechanistic rationale, which is organized based on the mode of chirality control.

1 Introduction

2 Substrate-Induced Asymmetric [1,2]-Stevens-Type Rearrangement

3 Catalyst-Controlled Asymmetric [1,2]-Stevens-Type Rearrangement

4 Conclusion and Outlook

Key words

[1,2]-Stevens rearrangement - metal carbenes - substrate-induced - asymmetric catalysis

Publication History

Received: 16 January 2023

Accepted after revision: 08 March 2023

Accepted Manuscript online:
08 March 2023

Article published online:
12 April 2023

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