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

被引：47

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

页码：4078 / 4081

页数：4

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