Novel chiral templates for 1,3-oxazolium-4-olate (isomunchnone) cycloadditions: (5R)- and (5S)-phenyloxazin-2,3-dione

被引：9

作者：

Angell, R

Drew, MGB

FenglerVeith, M

Finch, H

Harwood, LM

Jahans, AW

Tucker, TT

机构：

[1] UNIV READING,DEPT CHEM,READING RG6 6AD,BERKS,ENGLAND

[2] UNIV OXFORD,DYSON PERRINS LAB,OXFORD OX1 3QY,ENGLAND

[3] GLAXO WELLCOME INC,MED RES CTR,STEVENAGE SG1 2NY,HERTS,ENGLAND

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 17期

基金：

英国工程与自然科学研究理事会;

关键词：

RHODIUM CARBENOIDS; CONVERGENT APPROACH; CYCLIZATION; CYCLOPROPANATION;

D O I：

10.1016/S0040-4039(97)00557-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cycloadducts (4-10) were synthesised From isomunchnone derivatives of (5R)- and (SS)-phenyloxazin-2,3-dione by rhodium(II)-catalysed decomposition. High endo/exo-selectivities for additions to carbon-carbon dipolarophiles were observed. (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：3107 / 3110

页数：4

相关论文

共 20 条

[1] CHEMOSELECTIVITY OF RHODIUM CARBENOIDS - A COMPARISON OF THE SELECTIVITY FOR O-H INSERTION REACTIONS OR CARBONYL YLIDE FORMATION VERSUS ALIPHATIC AND AROMATIC C-H INSERTION AND CYCLOPROPANATION [J].

COX, GG ;

MOODY, CJ ;

AUSTIN, DJ ;

PADWA, A .

TETRAHEDRON, 1993, 49 (23) :5109-5126

[2] A CONVERGENT APPROACH TOWARD THE TIGLIANE RING-SYSTEM [J].

DAUBEN, WG ;

DINGES, J ;

SMITH, TC .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (27) :7635-7637

[3] ENANTIOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACID DERIVATIVES VIA THE STEREOSELECTIVE ALKYLATION OF A HOMOCHIRAL GLYCINE ENOLATE SYNTHON [J].

DELLARIA, JF ;

SANTARSIERO, BD .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (16) :3916-3926

[4] EFFECTS OF SECONDARY INTERACTIONS ON THE STEREOCHEMICAL OUTCOME OF RHODIUM(II) CARBOXYLATE CATALYZED CYCLOPROPANATION OF OLEFINS [J].

DEMONCEAU, A ;

NOELS, AF ;

HUBERT, AJ .

TETRAHEDRON, 1990, 46 (11) :3889-3896

[5] CATALYTIC METHODS FOR METAL CARBENE TRANSFORMATIONS [J].

DOYLE, MP .

CHEMICAL REVIEWS, 1986, 86 (05) :919-939

[6] Highly enantioselective intramolecular cyclopropanation reactions of N-allylic-N-methyldiazoacetamides catalyzed by chiral dirhodium(II) carboxamidates [J].

Doyle, MP ;

Kalinin, AV .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (06) :2179-2184

[7]

DOYLE MP, 1990, J AM CHEM SOC, V112, P1960

[8]

FRIEDRICHSEN W, 1988, TETRAHEDRON LETT, V29, P2045

[9] 1,3-DIPOLAR CYCLOADDITION OF ANHYDRO-4-HYDROXY-1,3-OXAZOLIUM HYDROXIDES WITH CARBONYL-COMPOUNDS [J].

HAMAGUCHI, M .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (06) :247-248

[10] A novel synthetic route to morpholin-2,3-diones from 2-aminoalcohols. [J].

Harwood, LM ;

Tucker, TT ;

Angell, R ;

Finch, H .

TETRAHEDRON LETTERS, 1996, 37 (24) :4217-4220