Addition Reactions of Chloro- or Iodomethyllithium to Imines. Synthesis of Enantiopure Aziridines and β-Chloroamines

被引：38

作者：

Concellon, Jose M. ^{[1
]}

Rodriguez-Solla, Humberto ^{[1
]}

Bernad, Pablo L. ^{[1
]}

Simal, Carmen ^{[1
]}

机构：

[1] Univ Oviedo, Fac Quim, Dept Quim Organ & Inorgan, E-33071 Oviedo, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 06期

关键词：

AZA-DARZENS REACTION; FUNCTIONALIZED ORGANOLITHIUM COMPOUNDS; HIGHLY DIASTEREOSELECTIVE SYNTHESIS; ASYMMETRIC RADICAL ADDITIONS; CARBOXYLIC-ACID CHLORIDES; ONE-POT TRANSFORMATION; IN-SITU; N-DIPHENYLPHOSPHINYLIMINES; OLEFIN AZIRIDINATION; STEREOSELECTIVE C-2;

D O I：

10.1021/jo802596y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a novel, simple, and efficient synthesis of aziridines and 1-chloroalkan-2-amines by the reaction of imines derived from various aldehydes and p-toluenesulfonamide or benzenesulfonamide with iodoor chloromethyllithium, respectively. Both halogenated anions were generated in situ by treatment of diiodo- or chloroiodomethane with methyllithium at -78 or 0 degrees C. The reaction of in situ generated iodo- or chloromethyllithium could also be performed from chiral 2-aminoaldimines to yield enantiopure aziridines or (2S,3S)-2,3-diamino-1-chloroalkanes with high stereoselectivity.

引用

页码：2452 / 2459

页数：8

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