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Synthesis 2023; 55(14): 2118-2127
DOI: 10.1055/a-2050-4967
DOI: 10.1055/a-2050-4967
short review
Special Issue Honoring Prof. Guoqiang Lin’s Contributions to Organic Chemistry
Recent Advances in Asymmetric [1,2]-Stevens-Type Rearrangement via Metal Carbenes
We are grateful for the financial support from the National Natural Science Foundation of China (22125108, 92056104), Yunnan Normal University, and Applied Basic Research Projects of Yunnan Province (202101AT070217).
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
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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For recent selected reviews on carbene chemistry, see:
For recent reviews on ynamide reactivity, see:
For recent reviews on the selenonium ylide, see:
For a recent non-enantioselective example on the selenonium ylide, see: