A novel rearrangement of N-Propargyl vinylaziridines. Mechanistic diversity in the aza-[2,3]-Wittig rearrangement

被引：22

作者：

Ahman, J ^{[1
]}

Somfai, P ^{[1
]}

机构：

[1] LUND UNIV,INST TECHNOL,CTR CHEM & CHEM ENGN,S-22100 LUND,SWEDEN

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 14期

关键词：

D O I：

10.1016/0040-4039(96)00302-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Propargyl vinylaziridines 4a-c have been prepared. The anionic rearrangement of 4a,b gives the trans-2,6-disubstituted tetrahydropyridines 5a,b, respectively, as the major products while 4c gives 1-pyrroline 7c exlusively. The mechanism for the formation of pyrrolines in these reactions is discussed. Copyright (C) 1996 Elsevier Science Ltd.

引用

页码：2495 / 2498

页数：4

共 17 条

[1] AHMAN J, 1994, J AM CHEM SOC, V116, P9781
[2] AN IMPROVED PROCEDURE FOR THE N-ALKYLATION OF AZIRIDINES
AHMAN, J
SOMFAI, P
[J]. SYNTHETIC COMMUNICATIONS, 1994, 24 (08) : 1121 - 1127
[3] ENANTIOSELECTIVE TOTAL SYNTHESIS OF (-)-INDOLIZIDINES 209B AND 209D VIA A HIGHLY EFFICIENT AZA-[2,3]-WITTIG REARRANGEMENT OF VINYLAZIRIDINES
AHMAN, J
SOMFAI, P
[J]. TETRAHEDRON, 1995, 51 (35) : 9747 - 9756
[4] BARTH H, 1979, HELV CHIM ACTA, V62, P1231, DOI 10.1002/hlca.19790620434
[5] SYNTHESIS OF 4-PHENYLPIPERIDINES BY TANDEM WITTIG OLEFINATION-AZA-WITTIG REARRANGEMENT OF 2-BENZOYLAZIRIDINES
COLDHAM, I
COLLIS, AJ
MOULD, RJ
RATHMELL, RE
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (21): : 2739 - 2745
[6] GAWLEY RE, 1991, COMPREHENSIVE ORGANI, V3
[7] FORMATION OF FURYLPYRROLIDINES AND FURYLPIPERIDINES ON HEATING L-PROLINE WITH REDUCING SUGARS AND FURANCARBOXALDEHYDES
HELAK, B
KERSTEN, E
SPENGLER, K
TRESSL, R
REWICKI, D
[J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1989, 37 (02) : 405 - 410
[8] WHY IS A VINYL ANION CONFIGURATIONALLY STABLE BUT A VINYL RADICAL CONFIGURATIONALLY UNSTABLE
JENKINS, PR
SYMONS, MCR
BOOTH, SE
SWAIN, CJ
[J]. TETRAHEDRON LETTERS, 1992, 33 (24) : 3543 - 3546
[9] Marshall J. A., 1991, COMPREHENSIVE ORGANI, V3
[10] ACYCLIC DIASTEREOSELECTION IN THE [2,3] WITTIG SIGMATROPIC REARRANGEMENT OF A SERIES OF ISOMERIC CROTYL ETHERS - A CONCEPTUAL-MODEL FOR THE TRANSITION-STATE GEOMETRY
MIKAMI, K
KIMURA, Y
KISHI, N
NAKAI, T
NAKAI, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (02) : 279 - 281

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