Enoldiazosulfones for Highly Enantioselective [3+3]-Cycloaddition with Nitrones Catalyzed by Copper(I) with Chiral BOX Ligands

被引：23
|
作者：
Adly, Frady G. [1 ,2 ]
Marichev, Kostiantyn O. [1 ]
Jensen, Joseph A. [1 ]
Arman, Hadi [1 ]
Doyle, Michael P. [1 ]
机构：
[1] Univ Texas San Antonio, Dept Chem, San Antonio, TX 78249 USA
[2] Univ Canberra, Fac Sci & Technol, Canberra, ACT 2601, Australia
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 01期
基金：
美国国家科学基金会;
关键词：
H INSERTION REACTIONS; BIS(OXAZOLINE) LIGANDS; CYCLOADDITION REACTIONS; CHEMISTRY; DIAZOSULFONES; HETEROCYCLE; SULFONES; ENOLDIAZOACETAMIDES; CYCLOPROPANATION; COMPLEXES;
D O I：
10.1021/acs.orglett.8b03421
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Enoldiazosulfones undergo [3 + 3]-cyclo-addition with nitrones when catalyzed by copper (I) catalysts, but not with dirhodium (II) catalysts. Under mild reaction conditions with chiral bisoxazoline ligands, copper (I) catalysts produce 1,2-oxazine-sulfone derivatives in high yields and enantioselectivities. Dirhodium (II) catalysts form stable donor acceptor cyclopropenes that undergo uncatalyzed [3 + 2]-cycloaddition reactions with nitrones.
引用
收藏
页码：40 / 44
页数：5
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