Asymmetric NHC-Catalyzed Redox α-Amination of α-Aroyloxyaldehydes

被引：52
|
作者：
Taylor, James E. [1 ]
Daniels, David S. B. [1 ]
Smith, Andrew D. [1 ]
机构：
[1] Univ St Andrews, Sch Chem, EaStCHEM, St Andrews KY16 9ST, Fife, Scotland
来源：
ORGANIC LETTERS | 2013年 / 15卷 / 23期
基金：
欧洲研究理事会; 英国工程与自然科学研究理事会;
关键词：
DIELS-ALDER REACTIONS; AMINO-ACIDS; CARBONYL-COMPOUNDS; ENANTIOSELECTIVE SYNTHESIS; ACTIVATION; ALDEHYDES; ESTERS; FUNCTIONALIZATION; ORGANOCATALYSIS; CONSTRUCTION;
D O I：
10.1021/ol402955f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Asymmetric alpha-amination through an N-heterocyclic carbene (NHC)-catalyzed redox reaction of alpha-aroyloxyaldehydes with N-aryl-N-aroyldiazenes to form alpha-hydrazino esters with high enantioselectivity (up to 99% ee) is reported. The hydrazide products are readily converted into enantioenriched N-aryl amino esters through samarium(II) iodide mediated N-N bond cleavage.
引用
收藏
页码：6058 / 6061
页数：4
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