On the acylation reactions of aza-allyl carbanions derived from N-[bis(methylthio)methylene]glycine ethyl ester and N-[bis(methylthio)methylene] benzylamine

被引：3

作者：

AlvarezIbarra, C

Csaky, AG

MartinezSantos, E

Quiroga, ML

机构：

[1] Depto. de Quimica Orgánica, Universidad Complutense, Ciudad Universitaria, s/n

来源：

TETRAHEDRON | 1997年 / 53卷 / 10期

关键词：

D O I：

10.1016/S0040-4020(97)00091-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New aspects of the acylation reaction of the aza-allyl anions derived from 1 and 2 have been studied. Under suitable reaction conditions, oxazoles 5, alpha,alpha-disubstituted alpha-acyl-alpha-amino acid derivatives 3, and alpha,beta-didehydroamino acid derivatives 7 can be prepared. A new 1,3-diamino-2-propanol derivative 8 was isolated by reaction of the C-acyl intermediate derived from N-[bis(methylthio)methylene]- benzylamine 2 and the anion 2 through an in situ addition-cyclocondensation tandem reaction. (C) 1997 Elsevier Science Ltd.

引用

页码：3679 / 3692

页数：14

共 35 条

[21] IBARRA CA, 1987, TETRAHEDRON LETT, V28, P6667
[22] IBARRA CA, 1995, J ORG CHEM, V60, P7934
[23] IBARRA CA, 1988, HETEROCYCLES, V27, P2177
[24] STRUCTURE AND REACTIVITY OF ALKALI-METAL ENOLATES
JACKMAN, LM
LANGE, BC
[J]. TETRAHEDRON, 1977, 33 (21) : 2737 - 2769
[25] VICINAL PROTON COUPLING IN NUCLEAR MAGNETIC RESONANCE
KARPLUS, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (18) : 2870 - 2871
[26] VITAMIN-B6 CATALYZED-REACTIONS OF ALPHA-AMINO AND ALPHA-KETO ACIDS - MODEL SYSTEMS
MARTELL, AE
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (04) : 115 - 124
[27] HIGHLY STEREOSELECTIVE ALDOL CONDENSATION USING AN ENANTIOSELECTIVE CHIRAL ENOLATE
MASAMUNE, S
ALI, SA
SNITMAN, DL
GARVEY, DS
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1980, 19 (07): : 557 - 558
[28] MULZER J, 1994, ANGEW CHEM INT EDIT, V33, P1737, DOI 10.1002/anie.199417371
[29] NODA K, 1983, PEPTIDES, V5
[30] O'Donnell M. J., 1988, TETRAHEDRON, V44, P5253

← 1 2 3 4 →