Tandem Insertion-[1,3]-Rearrangement: Highly Enantioselective Construction of α-Aminoketones

被引：45
作者：
Chen, Yushuang [1 ]
Liu, Yun [1 ]
Li, Zhaojing [1 ]
Dong, Shunxi [1 ]
Liu, Xiaohua [1 ]
Feng, Xiaoming [1 ]
机构：
[1] Sichuan Univ, Coll Chem, Key Lab Green Chem & Technol, Minist Educ, Chengdu 610064, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2020年 / 59卷 / 21期
基金：
中国国家自然科学基金;
关键词：
1,3]-rearrangement; asymmetric synthesis; bimetallic catalysis; tandem reaction; alpha-aminoketone; TO-C REARRANGEMENT; CLAISEN REARRANGEMENT; 1,3 O; ASYMMETRIC-SYNTHESIS; MIGRATION REACTIONS; RELAY CATALYSIS; AMINO KETONES; ALCOHOLS; ROUTE; BONDS;
D O I：
10.1002/anie.201914645
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An enantioselective synthesis of alpha-aminoketone derivatives were readily available through a tandem insertion[1,3] O-to-C rearrangement reaction. The rhodium salt and chiral N,N'-dioxide-indium(III) complex make up relay catalysis, which enables the O-H insertion of benzylic alcohols to N-sulfonyl-1,2,3-triazoles, and asymmetric [1,3]-rearrangement of amino enol ether intermediates, subsequently. Preliminary mechanistic studies suggested that the [1,3] O-to-C rearrangement step proceeded through an ion pair pathway.
引用
收藏
页码：8052 / 8056
页数：5
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