Enantioselective, Stereodivergent Hydroazidation and Hydroamination of Allenes Catalyzed by Acyclic Diaminocarbene (ADC) Gold(I) Complexes

被引：76
|
作者：
Khrakovsky, Dimitri A. [1 ]
Tao, Chuanzhou [1 ,2 ]
Johnson, Miles W. [1 ,3 ]
Thornbury, Richard T. [1 ]
Shevick, Sophia L. [1 ]
Toste, F. Dean [1 ]
机构：
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
[2] Huaihai Inst Technol, Sch Chem Engn, Lianyungang 222005, Peoples R China
[3] CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 20期
关键词：
acyclic diaminocarbene; enantioselective synthesis; gold catalysis; hydroamination; hydroazidation; ALLYLIC AZIDES; INTERMOLECULAR HYDROAMINATION; ASYMMETRIC-SYNTHESIS; CONJUGATE ADDITION; AZIDATION; CARBENES; LIGANDS; REGIO; CYCLOADDITIONS; REARRANGEMENT;
D O I：
10.1002/anie.201601550
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The gold-catalyzed enantioselective hydroazidation and hydroamination reactions of allenes are presented herein. ADC gold(I) catalysts derived from BINAM were critical for achieving high levels of enantioselectivity in both transformations. The sense of enantioinduction is reversed for the two different nucleophiles, allowing access to both enantiomers of the corresponding allylic amines using the same catalyst enantiomer.
引用
收藏
页码：6079 / 6083
页数：5
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