STEREOCONTROLLED DIELS-ALDER REACTIONS WITH CHIRAL TRICYCLIC OXAZOLIDINONES

被引：23

作者：

TANAKA, K

UNO, H

OSUGA, H

SUZUKI, H

机构：

[1] Department of Chemistry, Faculty of Science, Kyoto University, Sakyo, Kyoto, 606, Kitashirakawa

来源：

TETRAHEDRON-ASYMMETRY | 1993年 / 4卷 / 04期

关键词：

D O I：

10.1016/S0957-4166(00)80165-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

(1R,2R,6S,7S)-5-Aza-1,10,10-trimethyl-3-oxatricyclo[5.2.1.02,6]decan-4-one (endo-oxazolidinone) and (1R,2S,6R,7S)-isomer (exo-oxazolidinone) are found to be efficient diastereomeric auxiliaries for Diels-Alder reactions, which are promoted by Lewis acid catalysts with predictable absolute stereochemistry. Thus, the reaction of cyclopentadiene with N-crotonyl- or N-cinnamoyl-endo-oxazolidinones gave (1R,2R,3S,4S)-3-methyl- or (1R,2S,3S,4S)-3-phenylbicyclo[2.2.1]hept-5-ene-2-carboxylates, while their enantiomers, i.e. (1S,2S,3R,4R)-3-methyl- or (1S,2R,3R,4R)-3-phenylbicyclo[2.2.1]hept-5-ene-2-carboxylates were obtained stereoselectively from the corresponding exo-oxazolidinone derivatives.

引用

收藏

页码：629 / 632

页数：4

相关论文

共 32 条

[1] ASYMMETRIC-SYNTHESIS OF EXO-NORBORNANE-2-CARBOXYLIC ACIDS [J].

AVENOZA, A ;

BUENO, MP ;

CATIVIELA, C ;

MAYORAL, JA .

TETRAHEDRON-ASYMMETRY, 1992, 3 (03) :343-346

[2] ENANTIOSPECIFIC PREPARATION OF [(2R, 6S)-ENDO]-5-AZA-1,10,10-TRIMETHYL-3-OXATRICYCLO[5.2.1.0(2,6)]DECAN-4-ONE BY A NITRENE-MEDIATED ROUTE FROM [(1S)-ENDO]-(-)-BORNEOL AND ITS UTILITY AS A CHIRAL AUXILIARY IN SOME ASYMMETRIC TRANSFORMATIONS [J].

BANKS, MR ;

BLAKE, AJ ;

CADOGAN, JIG ;

DAWSON, IM ;

GOSNEY, I ;

GRANT, KJ ;

GAUR, S ;

HODGSON, PKG ;

KNIGHT, KS ;

SMITH, GW ;

STEVENSON, DE .

TETRAHEDRON, 1992, 48 (37) :7979-8006

[3] TOWARD THE DEVELOPMENT OF A GENERAL CHIRAL AUXILIARY .1. PREPARATION OF A NEW CLASS OF CAMPHOR LACTAM IMIDES AND THEIR APPLICATION TO THE CONSTRUCTION OF QUATERNARY CENTERS VIA DIELS-ALDER CYCLOADDITION [J].

BOECKMAN, RK ;

NELSON, SG ;

GAUL, MD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (06) :2258-2260

[4] HIGHLY ENANTIOSELECTIVE CATALYTIC DIELS-ALDER ADDITION PROMOTED BY A CHIRAL BIS(OXAZOLINE)-MAGNESIUM COMPLEX [J].

COREY, EJ ;

ISHIHARA, K .

TETRAHEDRON LETTERS, 1992, 33 (45) :6807-6810

[5] 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

[6] ASYMMETRIC-SYNTHESIS WITH LIGANDS .1. MODELS OF CHIRAL AUXILIARIES FOR ENANTIOSELECTIVE DIELS-ALDER REACTION [J].

GRAS, JL ;

PELLISSIER, H .

TETRAHEDRON LETTERS, 1991, 32 (48) :7043-7046

[7] 2-POINT-BINDING ASYMMETRIC DIELS-ALDER CATALYSTS - AROMATIC ALKYLDICHLOROBORANES [J].

HAWKINS, JM ;

LOREN, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (20) :7794-7795

[8]

HELMCHEN G, 1987, TETRAHEDRON LETT, V28, P83

[9] CATALYTIC ASYMMETRIC DIELS-ALDER REACTIONS [J].

KAGAN, HB ;

RIANT, O .

CHEMICAL REVIEWS, 1992, 92 (05) :1007-1019

[10] A BORATE PROPELLER COMPOUND AS CHIRAL CATALYST FOR AN ASYMMETRICALLY INDUCED DIELS-ALDER REACTION [J].

KAUFMANN, D ;

BOESE, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (05) :545-546

← 1 2 3 4 →