Palladium-Catalyzed Asymmetric Hydrosulfonylation of 1,3-Dienes with Sulfonyl Hydrazides

被引：84
作者：
Li, Ming-Ming [1 ,2 ]
Cheng, Lei [1 ,2 ]
Xiao, Li-Jun [1 ,2 ]
Xie, Jian-Hua [1 ,2 ]
Zhou, Qi-Lin [1 ,2 ]
机构：
[1] Nankai Univ, Coll Chem, State Key Lab, Tianjin 300071, Peoples R China
[2] Nankai Univ, Coll Chem, Inst Elementoorgan Chem, Tianjin 300071, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2021年 / 60卷 / 06期
基金：
中国国家自然科学基金;
关键词：
1; 3-dienes; asymmetric hydrosulfonylation; chiral sulfones; palladium; sulfonyl hydrazides; PRIMARY ALLYLIC AMINES; ALLENES; ALKYNES; SUBSTITUTION; ALCOHOLS;
D O I：
10.1002/anie.202012485
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A highly enantio- and regioselective hydrosulfonylation of 1,3-dienes with sulfonyl hydrazides has been realized by using a palladium catalyst containing a monodentate chiral spiro phosphoramidite ligand. The reaction provided an efficient approach to synthetically useful chiral allylic sulfones. Mechanistic studies suggest that the reaction proceeds through the formation of an allyl hydrazine intermediate and subsequent rearrangement to the chiral allylic sulfone product. The transformation of the allyl hydrazine intermediate to the product is the enantioselectivity-determining step.
引用
收藏
页码：2948 / 2951
页数：4
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