EXPLOITING STERIC SHIELDING - TUNING TERPENOID-DERIVED OXAZOLIDIN-2-ONES AS CHIRAL AUXILIARIES FOR THE DIELS-ALDER REACTION

被引:19
作者
BANKS, MR [1 ]
BLAKE, AJ [1 ]
BROWN, AR [1 ]
CADOGAN, JIG [1 ]
GAUR, S [1 ]
GOSNEY, I [1 ]
HODGSON, PKG [1 ]
THORBURN, P [1 ]
机构
[1] BP INT LTD,CTR RES & ENGN,SUNBURY TW16 7LN,MIDDX,ENGLAND
关键词
D O I
10.1016/0040-4039(94)85088-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Preparative methodology is described for access to three different terpenoid-derived oxazolidin-2-ones 4, 8, and 11, of which the latter, obtained from camphene in four steps, provides virtually complete asymmetric induction when acting as a chiral auxiliary in Diels-Alder cycloaddition reactions with cyclopentadiene.
引用
收藏
页码:489 / 492
页数:4
相关论文
共 11 条
[1]   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
[2]   PREPARATION OF CHIRAL 1-DEUTERIOBENZENEMETHANETHIOLS BY USING ALPHA',BETA-ELIMINATION OF CARBANIONS DERIVED FROM BENZYLIC THIOETHERS [J].
BIELLMANN, JF ;
DORCHYMONT, H .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (15) :2882-2886
[3]  
BROWN RFC, 1980, ORGANIC CHEM MONOGRA, V41
[4]  
CLANCY M, 1982, J CHEM RES-S, P78
[5]  
Evans D. A., 1982, ALDRICHIM ACTA, V15, P23
[6]   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
[7]   CHIRAL ENOLATE DESIGN [J].
EVANS, DA ;
TAKACS, JM ;
MCGEE, LR ;
ENNIS, MD ;
MATHRE, DJ ;
BARTROLI, J .
PURE AND APPLIED CHEMISTRY, 1981, 53 (06) :1109-1127
[8]   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
[9]   CAMPHOR-DERIVED N-ACRYLOYL AND N-CROTONOYL SULTAMS - PRACTICAL ACTIVATED DIENOPHILES IN ASYMMETRIC DIELS-ALDER REACTIONS [J].
OPPOLZER, W ;
CHAPUIS, C ;
BERNARDINELLI, G .
HELVETICA CHIMICA ACTA, 1984, 67 (05) :1397-1401
[10]   STEREOCONTROLLED DIELS-ALDER REACTIONS WITH CHIRAL TRICYCLIC OXAZOLIDINONES [J].
TANAKA, K ;
UNO, H ;
OSUGA, H ;
SUZUKI, H .
TETRAHEDRON-ASYMMETRY, 1993, 4 (04) :629-632