Cu(I)-Catalyzed Stereoselective Doyle-Kirmse Reaction

doi:10.6023/cjoc201704005

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (7): 1730-1740.DOI: 10.6023/cjoc201704005 Previous Articles Next Articles

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铜催化的立体选择性Doyle-Kirmse反应

盛哲^a,b, 马明^b, 彭玲玲^b, 张志坤^b, 褚长虎^a, 张艳^b, 王剑波^b

a. 华东理工大学药学院上海市新药设计重点实验室上海 200237;
b. 北京大学化学与分子工程学院教育部生物有机与分子工程重点实验室北京 100871

收稿日期:2017-04-05 修回日期:2017-04-23 发布日期:2017-05-04
通讯作者: 褚长虎, 王剑波 E-mail:chuch@ecust.edu.cn;wangjb@pku.edu.cn
基金资助:
国家自然科学基金（No.21332002）资助项目.

Cu(I)-Catalyzed Stereoselective Doyle-Kirmse Reaction

Sheng Zhe^a,b, Ma Ming^b, Peng Lingling^b, Zhang Zhikun^b, Chu Changhu^a, Zhang Yan^b, Wang Jianbo^b

a. Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, Shanghai 200237;
b. Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871

Received:2017-04-05 Revised:2017-04-23 Published:2017-05-04
Contact: 10.6023/cjoc201704005 E-mail:chuch@ecust.edu.cn;wangjb@pku.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No.21332002).

1. Cu(I)-Catalyzed Stereoselective Doyle-Kirmse Reaction.PDF(2370KB)

Abstract

A highly stereoselective[2,3]-σ rearrangement of sulfur ylide derived from Cu(I) carbene and allyl/propargyl sulfides (Doyle-Kirmse reaction) is reported. High stereocontrol is achieved by a dual asymmetric induction approach which involves a chiral auxiliary on diazo substrate, and steric bulky ligand of the Cu(I) catalyst. From mechanistic study, we suggest the[2,3]-σ rearrangement process occurs through free sulfur ylide intermediate. The reaction was further applied in kinetic resolution of allyl sulfide with a chiral center.

Key words: diazo compounds, carbene, sigmatropic rearrangement, sulfur ylide, asymmetric synthesis, chiral resolution

Cite this article

Sheng Zhe, Ma Ming, Peng Lingling, Zhang Zhikun, Chu Changhu, Zhang Yan, Wang Jianbo. Cu(I)-Catalyzed Stereoselective Doyle-Kirmse Reaction[J]. Chin. J. Org. Chem., 2017, 37(7): 1730-1740.

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铜催化的立体选择性Doyle-Kirmse反应

Cu(I)-Catalyzed Stereoselective Doyle-Kirmse Reaction

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