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Wang et al. Chem Synth 2023;3:12 Chemical Synthesis
DOI: 10.20517/cs.2023.01

Review Open Access

Application of sulfonium and sulfoxonium ylides in

organocatalyzed asymmetric reaction

1,2
1,*
1
1
1
1
Zhen-Hua Wang , Ting-Jia Sun , Yan-Ping Zhang , Yong You , Jian-Qiang Zhao , Jun-Qing Yin , Wei-
Cheng Yuan 1,2,*
1
Innovation Research Center of Chiral Drugs, Institute for Advanced Study, Chengdu University, Chengdu 610106, Sichuan,
China.
2
National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences,
Chengdu 610041, Sichuan, China.
* Correspondence to: Prof. Zhen-Hua Wang, Innovation Research Center of Chiral Drugs, Institute for Advanced Study,
Chengdu University, No. 2025 Chengluo Avenue, Chengdu 610106, Sichuan, China. E-mail: wangzhenhua@cdu.edu.cn; Prof.
Wei-Cheng Yuan, Innovation Research Center of Chiral Drugs, Institute for Advanced Study, Chengdu University, No. 2025
Chengluo Avenue, Chengdu 610106, Sichuan, China. E-mail: yuanwc@cioc.ac.cn
How to cite this article: Wang ZH, Sun TJ, Zhang YP, You Y, Zhao JQ, Yin JQ, Yuan WC. Application of sulfonium and
sulfoxonium ylides in organocatalyzed asymmetric reaction. Chem Synth 2023;3:12. https://dx.doi.org/10.20517/cs.2023.01
Received: 5 Jan 2023 First Decision: 16 Jan 2023 Revised: 8 Feb 2023 Accepted: 20 Feb 2023 Published: 1 Mar 2023

Academic Editor: Feng Shi Copy Editor: Ke-Cui Yang Production Editor: Ke-Cui Yang

Abstract
Sulfur-based ylides are very important and valuable reagents in organic synthesis and have been widely applied in
the preparation of cyclic compounds and the formation of C-X (X = C, N, O, S, B, P) bond. Since the early 2000s,
asymmetric organocatalysis has become a powerful strategy in organic synthesis (even highlighted by the 2021
Nobel Prize in Chemistry) and has attracted widespread research interest among synthetic organic chemists. In
this area, a large number of outstanding achievements have been registered in the novel chiral catalysts design,
new compounds synthesis, various reagents application, and versatile reaction discovery. Given the extensive
application of sulfonium and sulfoxonium ylides in organic synthesis, in this review, we mainly summarize the
organocatalyzed asymmetric reactions involving these ylide reagents as one of the reactants. Detailed reaction
mechanisms, transition states and some synthetic applications are highlighted. The challenges and opportunities of
this field are also discussed in the outlook.

Keywords: Asymmetric catalysis, organocatalysis, sulfonium ylides, sulfoxonium ylides, cyclization reaction

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