Generation and Diels-Alder reactions of t-butyl 2H-azirine-3-carboxylate

被引：31

作者：

Alves, MJ ^{[1
]}

Gilchrist, TL

机构：

[1] Univ Minho, Dept Quim, P-4710 Braga, Portugal

[2] Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 41期

关键词：

D O I：

10.1016/S0040-4039(98)01617-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The azirinyl ester 2 (R = Bu-t) has been generated by thermolysis of t-butyl 2-azidoacrylate. It is too unstable to allow its full characterisation but it has been intercepted by Diels-Alder cycloaddition to several dienes. Addition to a chiral diene 8 is highly diastereoselective. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：7579 / 7582

页数：4

相关论文

共 14 条

[1] Methyl 2-aryl-2H-azirine-3-carboxylates as dienophiles [J].

Alves, MJ ;

Gilchrist, TL .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (02) :299-303

[2]

ANDERSON DJ, 1975, SYNTHESIS-STUTTGART, P483

[3] ANALOGS OF SIALIC ACIDS AS POTENTIAL SIALIDASE INHIBITORS - SYNTHESIS OF 2-C-HYDROXYMETHYL DERIVATIVES OF N-ACETYL-6-AMINO-2,6-DIDEOXY-NEURAMINIC ACID [J].

BERNET, B ;

MURTY, ARCB ;

VASELLA, A .

HELVETICA CHIMICA ACTA, 1990, 73 (04) :940-958

[4] REACTIONS WITH PHOSPHINE ALKYLENES .23. PHOSPHINE ALKYLENE REACTIONS WITH NITRILE OXIDES . A NEW POTENTIAL SYNTHESIS FOR AZIRINES KETENIMINES AND ALPHA,BETA-UNSATURATED OXIMES [J].

BESTMANN, HJ ;

KUNSTMAN.R .

CHEMISCHE BERICHTE-RECUEIL, 1969, 102 (06) :1816-&

[5] A fast procedure for the preparation of amides/peptides from carboxylic acids and azides via two redox reactions: Application to the synthesis of methionine enkephalin [J].

Ghosh, SK ;

Verma, R ;

Ghosh, U ;

Mamdapur, VR .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1996, 69 (06) :1705-1711

[6] ASYMMETRIC DIELS-ALDER REACTIONS .2. A MODEL TO ACCOUNT FOR THE DIASTEREOFACIAL REACTIVITY OF (E)-1-(2',3',4',6'-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYLOXY)-3-TRIMETHYLSILOXYBUTA-1,3-DIENE AND ITS 2-METHYL DERIVATIVE - X-RAY MOLECULAR-STRUCTURE OF (E)-1-(2',3',4',6'-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYLOXY)-3-TRIMETHYLSILOXYBUTA-1,3-DIENE AND OF (1R,6R,9R,10S)-9-METHYL-10-(2',3',4',6'-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYLOXY)BICYCLO[4.4.0]DEC-3-ENE-2,5,8-TRIONEC [J].

GUPTA, RC ;

LARSEN, DS ;

STOODLEY, RJ ;

SLAWIN, AMZ ;

WILLIAMS, DJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (04) :739-749

[7] A GENERAL SYNTHESIS OF VINYL AZIDES FROM OLEFINS . STEREOCHEMISTRY OF ELIMINATION FROM BETA-IODO AZIDES [J].

HASSNER, A ;

FOWLER, FW .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (07) :2686-&

[8] VINYL AZIDES IN HETEROCYCLIC SYNTHESIS .3. ISOLATION OF AZIRINE TRIMERS (1,3,8-TRIAZATRICYCLO[4.3.0.03,5]NON-7-ENES) AND INTRAMOLECULAR INTERCEPTION OF NITRILE YLIDES BY NEIGHBORING PI-BONDS OR NUCLEOPHILES [J].

HICKEY, DMB ;

MOODY, CJ ;

REES, CW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (06) :1119-1122

[9] A SIMPLE SYNTHESIS OF 2-AZIDO-2-ALKENOATES [J].

KAKIMOTO, MA ;

KAI, M ;

KONDO, K .

CHEMISTRY LETTERS, 1982, (04) :525-526

[10]

KNITTEL D, 1985, SYNTHESIS-STUTTGART, P186