THERMAL AND LEWIS ACID-PROMOTED ASYMMETRIC HETERO-DIELS-ALDER REACTION OF A 1-THIABUTA-1,3-DIENE SYSTEM (THIOCHALCONE) WITH CHIRAL ACRYLIC ESTERS AND N-ACRYLOYL-CARBOXIMIDE AND N-CROTONYL-CARBOXIMIDE

被引：16

作者：

SAITO, T

KARAKASA, T

FUJI, H

FURUNO, E

SUDA, H

KOBAYASHI, K

机构：

[1] NIPPON DENT UNIV TOKYO,CHIYODA KU,TOKYO 102,JAPAN

[2] RIKEN,INST PHYS & CHEM RES,WAKO,SAITAMA 35101,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 11期

关键词：

D O I：

10.1039/p19940001359

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Thermal and Lewis acid-promoted asymmetric hetero Diels-Alder reactions of the thiabutadiene 1 with the chiral dienophiles 2-5 derived from (-)-menthol, (+)-borneol and (-)-4-benzyloxazolidinone affords the optically active dihydrothiopyran derivatives. The chiral induction is in the range 13-92% d.e. depending mainly upon the auxiliary chiral groups. The absolute configuration of the endo cycloadducts is confirmed by the derivatization based on X-ray crystallographic analysis.

引用

收藏

页码：1359 / 1362

页数：4

相关论文

共 15 条

[1] NEW ASYMMETRIC DIELS-ALDER CYCLOADDITION REACTIONS - CHIRAL ALPHA,BETA-UNSATURATED CARBOXIMIDES AS PRACTICAL CHIRAL ACRYLATE AND CROTONATE DIENOPHILE SYNTHONS [J].

EVANS, DA ;

CHAPMAN, KT ;

BISAHA, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (15) :4261-4263

[2] ASYMMETRIC DIELS-ALDER CYCLO-ADDITION REACTIONS WITH CHIRAL ALPHA, BETA-UNSATURATED N-ACYLOXAZOLIDINONES [J].

EVANS, DA ;

CHAPMAN, KT ;

BISAHA, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (04) :1238-1256

[3] ASYMMETRIC INDUCTION IN A 1,4-CYCLOADDITION REACTION . INFLUENCE OF VARIATION OF CONFIGURATION OF ASYMMETRIC CENTER [J].

FARMER, RF ;

HAMER, J .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (07) :2418-&

[4] FUNCTIONAL-GROUPS AT CONCAVE SITES - ASYMMETRIC DIELS-ALDER SYNTHESIS WITH ALMOST COMPLETE (LEWIS-ACID CATALYZED) OR HIGH (UNCATALYZED) STEREOSELECTIVITY [J].

HELMCHEN, G ;

SCHMIERER, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1981, 20 (02) :205-207

[5] INFLUENCE OF CATION COMPLEXING SOLVENT ADDITIVES AND FUNCTIONAL-GROUPS IN ASYMMETRIC ALKYLATIONS OF ESTERS VIA LITHIUM ENOLATES [J].

HELMCHEN, G ;

SELIM, A ;

DORSCH, D ;

TAUFER, I .

TETRAHEDRON LETTERS, 1983, 24 (31) :3213-3216

[6]

HELMCHEN G, 1986, MODERN SYNTHETIC MET, V4, P262

[7] LEWIS ACID-PROMOTED HETERO-DIELS-ALDER REACTION OF ALPHA,BETA-UNSATURATED THIOKETONES [J].

MOTOKI, S ;

SAITO, T ;

KARAKASA, T ;

MATSUSHITA, T ;

FURUNO, E .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (21) :2943-2948

[8] THERMAL AND LEWIS ACID-PROMOTED NOVEL ASYMMETRIC HETERO-DIELS-ALDER REACTIONS OF A 1-THIABUTA-1,3-DIENE SYSTEM (THIOCHALCONES) WITH (-)-DIMENTHYL FUMARATE [J].

MOTOKI, S ;

SAITO, T ;

KARAKASA, T ;

KATO, H ;

MATSUSHITA, T ;

HAYASHIBE, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (09) :2281-2283

[9] A REINVESTIGATION OF ASYMMETRIC INDUCTION IN DIELS-ALDER REACTIONS TO CHIRAL ACRYLATES [J].

OPPOLZER, W ;

KURTH, M ;

REICHLIN, D ;

MOFFATT, F .

TETRAHEDRON LETTERS, 1981, 22 (27) :2545-2548

[10] ASYMMETRIC DIELS-ALDER AND ENE REACTIONS IN ORGANIC-SYNTHESIS [J].

OPPOLZER, W .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (11) :876-889