Synthesis 2023; 55(23): 3895-3905
Recent Advances in the Asymmetric Doyle–Kirmse Reaction
Chong-Yang Shi
a
College of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650500, P. R. of China
,
Bo Zhou
b
Key Laboratory of Chemical Biology of Fujian Province and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, P. R. of China
,
Ming-Yu Teng∗
a
College of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650500, P. R. of China
,
Long-Wu Ye∗
a
College of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650500, P. R. of China
b
Key Laboratory of Chemical Biology of Fujian Province and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, P. R. of China
c
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
› Institutsangaben We are grateful for financial support from the National Natural Science Foundation of China (22125108), Yunnan Normal University, and the Applied Basic Research Foundation of Yunnan Province (202101AT070217).
Abstract
The asymmetric Doyle–Kirmse reaction has become increasingly important in the construction of chiral sulfides, especially for those with quaternary carbon stereocenters. Over the few past decades, a series of catalytic asymmetric approaches have been developed promoted by copper, rhodium, nickel, and other chiral catalysts. Apart from the frequently investigated sulfonium ylides, the enantioselective [2,3]-sigmatropic rearrangement of selenium ylides and iodonium ylides has also been discovered recently. This review summarizes recent advances in the asymmetric Doyle–Kirmse reaction according to the patterns of chirality induction. The synthetic methods for rearranged products, reaction mechanisms and applications are discussed in this review.
1 Introduction
2 Asymmetric Doyle–Kirmse Reaction Controlled by Chiral Free Ylides
3 Asymmetric Doyle–Kirmse Reaction Controlled by Chiral Metal-Bound Ylides
4 Conclusion and Outlook
Key words
Doyle–Kirmse reaction -
chiral free ylides -
chiral metal-bound ylides -
asymmetric catalysis
Publikationsverlauf
Eingereicht: 31. Mai 2023
© 2023. Thieme. All rights reserved
Georg Thieme Verlag KG
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