Noncovalent Organocatalytic Synthesis of Enantioenriched Terminal Aziridines with a Quaternary Stereogenic Center

被引：46
作者：
De Fusco, Claudia [1 ]
Fuoco, Tiziana [1 ]
Croce, Gianluca [2 ]
Lattanzi, Alessandra [1 ]
机构：
[1] Univ Salerno, Dipartimento Chim & Biol, I-84084 Fisciano, Italy
[2] Univ Piemonte Orientale, DISIT, I-15121 Alessandria, Italy
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 16期
关键词：
CATALYTIC ASYMMETRIC AZIRIDINATION; AZA-DARZENS REACTION; ALPHA-AMINO-ACIDS; ALPHA; BETA-UNSATURATED ALDEHYDES; ENANTIOSELECTIVE AZIRIDINATION; BIFUNCTIONAL ORGANOCATALYSTS; MICHAEL ADDITION; CONSTRUCTION; STEREOCENTERS; EPOXIDATION;
D O I：
10.1021/ol3017066
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A high-yielding and enantioselective access to novel N-Boc terminal aziridines, bearing a quaternary stereogenic center, has been developed via an aza-Michael initiated ring-closure (aza-MIRC) reaction of alpha-acyl acrylates with an N-tosyloxy tert-butyl carbamate catalyzed by a chiral amino thiourea. The feasibility of the aziridine regioselective ring-opening to valuable alpha,alpha-disubstituted alpha-amino acid esters has been demonstrated.
引用
收藏
页码：4078 / 4081
页数：4
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