HIGHLY EFFICIENT CHIRAL 2-OXAZOLIDINONE AUXILIARIES DERIVED FROM METHYLCYCLOPENTADIENES AND 2-OXAZOLONE

被引：46

作者：

HASHIMOTO, N ^{[1
]}

ISHIZUKA, T ^{[1
]}

KUNIEDA, T ^{[1
]}

机构：

[1] KUMAMOTO UNIV,FAC PHARMACEUT SCI,KUMAMOTO 862,JAPAN

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 05期

关键词：

D O I：

10.1016/S0040-4039(00)75800-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sterically congested [4+2]cycloadduct-based 2-oxazolidinones, (1R, 2R, 6S, 7S)-1, 7, 8, 9, 10, 10-hexamethyl- and(1S, 2R, 6S, 7S, 10R)-1, 7, 8, 9, 10, 10-pentamethyl-3-oxa-5-azatricyclo(5.2.1.0(2,6))dec-8-en-4-ones and their enantiomers, derived from hexamethyl- and pentamethylcyclopentadienes and 2-oxazolone, serve as extremely powerful chiral auxiliaries in the asymmetric alkylations and Diels-Alder reaction.

引用

收藏

页码：721 / 724

页数：4

相关论文

共 16 条

[1] ASYMMETRIC ALDOL REACTIONS EMPLOYING A CAMPHOR-DERIVED CHIRAL OXAZINONE AUXILIARY [J].

AHN, KH ;

LEE, SK ;

LIM, AK .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (19) :5065-5066

[2] ASYMMETRIC ALDOL REACTIONS - A NEW CAMPHOR-DERIVED CHIRAL AUXILIARY GIVING HIGHLY STEREOSELECTIVE ALDOL REACTIONS OF BOTH LITHIUM AND TITANIUM(IV) ENOLATES [J].

BONNER, MP ;

THORNTON, ER .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (04) :1299-1308

[3]

Evans D. A., 1982, ALDRICHIM ACTA, V15, P23

[4] 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

[5] TRANSITION-STATE PI-SOLVATION BY AROMATIC RINGS - AN ELECTRONIC CONTRIBUTION TO DIELS-ALDER REACTION DIASTEREOSELECTIVITY [J].

EVANS, DA ;

CHAPMAN, KT ;

HUNG, DT ;

KAWAGUCHI, AT .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (11) :1184-1186

[6] ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES [J].

EVANS, DA ;

BARTROLI, J ;

SHIH, TL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2127-2129

[7] ASYMMETRIC ALKYLATION REACTIONS OF CHIRAL IMIDE ENOLATES - A PRACTICAL APPROACH TO THE ENANTIOSELECTIVE SYNTHESIS OF ALPHA-SUBSTITUTED CARBOXYLIC-ACID DERIVATIVES [J].

EVANS, DA ;

ENNIS, MD ;

MATHRE, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (06) :1737-1739

[8] PRACTICAL PREPARATION OF CHIRAL 4-SUBSTITUTED 2-OXAZOLIDINONES [J].

ISHIZUKA, T ;

KIMURA, K ;

ISHIBUCHI, S ;

KUNIEDA, T .

CHEMISTRY LETTERS, 1992, (06) :991-994

[9] EXTREMELY POWERFUL CHIRAL AUXILIARIES - ENANTIOMERIC [4+2] CYCLOADDUCTS OF 2-OXAZOLONE AND 9,10-DIMETHYLANTHRACENE [J].

KIMURA, K ;

MURATA, K ;

OTSUKA, K ;

ISHIZUKA, T ;

HARATAKE, M ;

KUNIEDA, T .

TETRAHEDRON LETTERS, 1992, 33 (31) :4461-4464

[10]

MATSUNAGA H, 1992, CHEM PHARM BULL, V40, P1077