铜催化的立体选择性Doyle-Kirmse反应
收稿日期: 2017-04-05
修回日期: 2017-04-23
网络出版日期: 2017-05-04
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
Received date: 2017-04-05
Revised date: 2017-04-23
Online published: 2017-05-04
Supported by
Project supported by the National Natural Science Foundation of China (No.21332002).
盛哲 , 马明 , 彭玲玲 , 张志坤 , 褚长虎 , 张艳 , 王剑波 . 铜催化的立体选择性Doyle-Kirmse反应[J]. 有机化学, 2017 , 37(7) : 1730 -1740 . DOI: 10.6023/cjoc201704005
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.
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