Aziridine and azirine carboxylic esters

被引：39

作者：

Zwanenburg, B

Thijs, L

机构：

[1] Department of Organic Chemistry, NSR Ctr. Molec. Struct., Des. S., University of Nijmegen, Toernooiveld

来源：

PURE AND APPLIED CHEMISTRY | 1996年 / 68卷 / 03期

关键词：

D O I：

10.1351/pac199668030735

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A convenient synthesis of aziridine-2-carboxylic esters of high enantiopurity from the corresponding oxiranecarboxylic esters is described. Ring opening reactions of these aziridine esters with various nucleophilic agents constitute a versatile entree to functionalized amino acid derivatives. The synthesis of 2H-azirine-2-carboxylic esters from aziridine-2-carboxylic esters by an eliminative reaction is reported. An alternative preparation of 2H-azirine-2-carboxylic esters involves an alkaloid mediated synthesis from the oxime tosylates of beta-keto esters by a modified Neber reaction.

引用

页码：735 / 738

页数：4

共 18 条

[1]

DEYRUP JA, 1983, SMALL RING HETEROC 1, P11

[2]

FANTA PE, 1964, HETEROCYCLIC COMPO 1, P528

[3] CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION [J].

GAO, Y ;

HANSON, RM ;

KLUNDER, JM ;

KO, SY ;

MASAMUNE, H ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) :5765-5780

[4]

GENTILUCCI L, IN PRESS

[5]

LEGTERS J, 1992, RECL TRAV CHIM PAY B, V111, P75

[6]

LEGTERS J, 1992, RECL TRAV CHIM PAY B, V111, P69

[7]

LEGTERS J, 1992, RECL TRAV CHIM PAY B, V111, P59

[8]

LEGTERS J, 1992, RECL TRAV CHIM PAY B, V111, P1

[9]

LEGTERS J, 1992, RECL TRAV CHIM PAY B, V111, P211

[10] SYNTHESIS OF FUNCTIONALIZED PHENYLALANINE DERIVATIVES BY RING-OPENING REACTIONS OF 3-ARYLAZIRIDINE-2-CARBOXYLIC ESTERS [J].

LEGTERS, J ;

THIJS, L ;

ZWANENBURG, B .

RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS-JOURNAL OF THE ROYAL NETHERLANDS CHEMICAL SOCIETY, 1992, 111 (01) :16-21

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