REARRANGEMENT OF PRIMARY 2,3-EPOXY AMINES INTO 1,2-AZIRIDINYL 3-OLS

被引：24

作者：

NAJIME, R ^{[1
]}

PILARD, S ^{[1
]}

VAULTIER, M ^{[1
]}

机构：

[1] UNIV RENNES 1,PHYSICOCHIM STRUCT GRP,URA 704,CAMPUS BEAULIEU,AVE GEN LECLERC,F-35042 RENNES,FRANCE

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 37期

关键词：

2,3-EPOXY AMINES; 1,2-AZIRIDINYL 3-OLS; INTRAMOLECULAR RING OPENING; TRIMETHYLALUMINUM; REARRANGEMENT;

D O I：

10.1016/S0040-4039(00)79090-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Conditions were found to transform primary 2,3-epoxy amines into 1,2-aziridinyl 3-ols which involve an intramolecular opening of the epoxide ring mediated by trimethylaluminum.

引用

页码：5351 / 5354

页数：4

共 18 条

[1] RULES FOR RING-CLOSURE [J].

BALDWIN, JE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736

[2]

BARTNIK R, 1982, J CHEM RES-S, P287

[3]

Bartnik R., 1982, J CHEM RES M, P2701

[4] SELECTIVE TRANSFORMATION OF 2,3-EPOXY ALCOHOLS AND RELATED DERIVATIVES - STRATEGIES FOR NUCLEOPHILIC-ATTACK AT CARBON-1 [J].

BEHRENS, CH ;

KO, SY ;

SHARPLESS, KB ;

WALKER, FJ .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) :5687-5696

[5] SELECTIVE TRANSFORMATIONS OF 2,3-EPOXY ALCOHOLS AND RELATED DERIVATIVES - STRATEGIES FOR NUCLEOPHILIC-ATTACK AT CARBON-3 OR CARBON-2 [J].

BEHRENS, CH ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) :5696-5704

[6] NUCLEOPHILIC OPENING OF CHIRAL BIS(AZIRIDINES) - A ROUTE TO ENANTIOMERICALLY PURE ALPHA-AMINO ALDEHYDES OR ACIDS AND POLYSUBSTITUTED PIPERIDINES [J].

DUREAULT, A ;

TRANCHEPAIN, I ;

DEPEZAY, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (22) :5324-5330

[7] A NEW ACCESS TO CHIRAL AZIRIDINES BY ENZYMATIC TRANSESTERIFICATION OF MESO-BIS(ACETOXYMETHYL)AZIRIDINES [J].

FUJI, K ;

KAWABATA, T ;

KIRYU, Y ;

SUGIURA, Y ;

TAGA, T ;

MIWA, Y .

TETRAHEDRON LETTERS, 1990, 31 (46) :6663-6666

[8] ENANTIOSPECIFIC SYNTHESIS OF AN AZIRIDINOBENZOAZOCINONE, AN ADVANCED INTERMEDIATE CONTAINING THE CORE NUCLEUS OF FR900482 AND FK973 [J].

JONES, RJ ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (04) :1144-1146

[9] SYNTHESIS OF SACCHARIDES AND RELATED POLYHYDROXYLATED NATURAL-PRODUCTS .1. SIMPLE ALDITOLS [J].

KATSUKI, T ;

LEE, AWM ;

MA, P ;

MARTIN, VS ;

MASAMUNE, S ;

SHARPLESS, KB ;

TUDDENHAM, D ;

WALKER, FJ .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (07) :1373-1378

[10]

KNOUZI N, 1985, B SOC CHIM FR, P815

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