ELECTROPHILIC AMINATION - PREPARATION AND USE OF N-BOC-3-(4-CYANOPHENYL)OXAZIRIDINE, A NEW REAGENT THAT TRANSFERS A N-BOC GROUP TO N-NUCLEOPHILES AND C-NUCLEOPHILES

被引：90

作者：

VIDAL, J ^{[1
]}

GUY, L ^{[1
]}

STERIN, S ^{[1
]}

COLLET, A ^{[1
]}

机构：

[1] ECOLE NORMALE SUPER LYON,CNRS,UMR 117,46 ALLEE ITALIE,F-69364 LYON 07,FRANCE

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 18期

关键词：

D O I：

10.1021/jo00070a007

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe the preparation of the title compound 2b via aza-Wittig reaction of N-Boc-triphenyliminophosphorane (6) with 4-cyanobenzaldehyde followed by Oxone oxidation of the resulting imine 5b. Oxaziridine 2b is a stable, crystalline solid, which transfers under mild conditions its N-Boc fragment to primary and secondary amines (to give N(beta)-Boc-hydrazines) and enolates (to give N-Boc-amino derivatives).

引用

页码：4791 / 4793

页数：3

共 26 条

[1]

AMOUR A, UNPUB

[2]

ANDREAE S, 1991, SYNTHESIS-STUTTGART, P327

[3] SYNTHESES AND REARRANGEMENTS OF SPIROCYCLIC OXAZIRIDINES DERIVED FROM UNSYMMETRICAL KETONES [J].

AUBE, J ;

HAMMOND, M ;

GHERARDINI, E ;

TAKUSAGAWA, F .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :499-508

[4] X-RAY CONFORMATIONAL STUDY OF HYDRAZINO PEPTIDE ANALOGS [J].

AUBRY, A ;

BAYEUL, D ;

MANGEOT, JP ;

VIDAL, J ;

STERIN, S ;

COLLET, A ;

LECOQ, A ;

MARRAUD, M .

BIOPOLYMERS, 1991, 31 (06) :793-801

[5] ENANTIOMERIC ALPHA-AMINOPROPIOPHENONES (CATHINONE) - PREPARATION AND INVESTIGATION [J].

BERRANG, BD ;

LEWIN, AH ;

CARROLL, FI .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (13) :2643-2647

[6]

BODANSZKY M, 1984, PRACTICE PEPTIDE SYN, P242

[7] A SIMPLE CONVERSION OF 1-CHLOROETHYL CARBONATES TO FLUOROFORMATES - VALUE IN THE PREPARATION OF TERTIARY ALKYL FLUOROFORMATES [J].

DANG, VA ;

OLOFSON, RA ;

WOLF, PR ;

PITEAU, MD ;

SENET, JPG .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) :1847-1851

[8] ASYMMETRIC HYDROXYLATION OF ENOLATES WITH N-SULFONYLOXAZIRIDINES [J].

DAVIS, FA ;

CHEN, BC .

CHEMICAL REVIEWS, 1992, 92 (05) :919-934

[9] APPLICATIONS OF OXAZIRIDINES IN ORGANIC-SYNTHESIS [J].

DAVIS, FA ;

SHEPPARD, AC .

TETRAHEDRON, 1989, 45 (18) :5703-5742

[10]

DECORTE E, 1980, Acta Pharmaceutica Jugoslavica, V30, P183

← 1 2 3 →