Recent Advances in the Asymmetric Doyle–Kirmse Reaction

Chong-Yang Shi; Bo Zhou; Ming-Yu Teng; Long-Wu Ye

doi:10.1055/a-2119-5390

Synthesis, Inhaltsverzeichnis

Synthesis 2023; 55(23): 3895-3905
DOI: 10.1055/a-2119-5390

short review

Recent Advances in the Asymmetric Doyle–Kirmse Reaction

Autor*innen

Chong-Yang Shi

^aCollege of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650500, P. R. of China
Bo Zhou

^bKey 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∗

^aCollege of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650500, P. R. of China
Long-Wu Ye∗

^aCollege of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650500, P. R. of China

^bKey Laboratory of Chemical Biology of Fujian Province and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, P. R. of China

^cState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China

Abstract

Alle Artikel dieser Rubrik

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

Volltext

Referenzen

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