STEREOSELECTIVE CYCLOADDITION OF NITRILE OXIDES TO 4-VINYL-OXAZOLINES AND 4-VINYL-OXAZOLIDINES

被引：19

作者：

BOYD, EC ^{[1
]}

PATON, RM ^{[1
]}

机构：

[1] UNIV EDINBURGH,DEPT CHEM,W MAINS RD,EDINBURGH EH9 3JJ,MIDLOTHIAN,SCOTLAND

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 19期

关键词：

1,3-DIPOLAR CYCLOADDITION; NITRILE OXIDES; ISOXAZOLINES;

D O I：

10.1016/S0040-4039(00)93409-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cycloaddition of nitrile oxides to 4-vinyl-2-oxazoline 1 and to 4-vinyloxazolidine 2 afford diastereomeric mixtures of 2-isoxazolines in which the erythro product predominates (32-64% d.e.). In contrast, the corresponding reactions with acyclic analogue 3 favoured the threo-adducts and were less selective (8-20% d.e.).

引用

页码：3169 / 3172

页数：4

共 19 条

[1]

ANNUNZIATA R, 1989, GAZZ CHIM ITAL, V119, P253

[2]

BLAKE AJ, 1991, CARBOHYD RES, V216, P461

[3]

BLAKE AJ, UNPUB

[4]

Caramella P., 1984, 1 3 DIPOLAR CYCLOADD

[5] CHLORINATION OF OXIMES .1. REACTION AND MECHANISM OF CHLORINATION OF OXIMES IN COMMERCIAL CHLOROFORM AND METHYLENE CHLORIDE [J].

CHIANG, YH .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (15) :2146-&

[6]

CURRAN DP, 1988, ADV CYCLOADDITION, V1, P129

[7] SYNTHESIS OF C-DISACCHARIDES USING NITRILE OXIDE CYCLO-ADDITION CHEMISTRY [J].

DAWSON, IM ;

JOHNSON, T ;

PATON, RM ;

RENNIE, RAC .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (19) :1339-1340

[8]

DEAMICI M, 1989, J ORG CHEM, V54, P193

[9]

FUSHIWA S, 1987, CHEM LETT, P2085

[10] THE SYNTHESIS AND CONFIGURATIONAL STABILITY OF DIFFERENTIALLY PROTECTED BETA-HYDROXY-ALPHA-AMINO ALDEHYDES [J].

GARNER, P ;

PARK, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (12) :2361-2364

← 1 2 →