REACTIONS OF A NEW OPTICALLY-ACTIVE ARYLPERHYDRONAPHTHALENOL BASED CHIRAL AUXILIARY

被引:10
作者
HAMON, DPG [1 ]
HOLMAN, JW [1 ]
MASSYWESTROPP, RA [1 ]
机构
[1] UNIV ADELAIDE,DEPT AGR SCI & RURAL DEV,GPO BOX 498,ADELAIDE,SA 5001,AUSTRALIA
关键词
D O I
10.1016/S0957-4166(00)86053-X
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
(1R,4aS,8S,8aS)-8-(5'-methoxy-2'-methylphenyl)-8-methyldecahydro-1-naphthalenol is a chiral auxiliary more efficient than 8-phenylmenthol in the Diels-Alder reaction of its acrylate ester with cyclopentadiene and in the diisobutylaluminium hydride reduction of its phenylglyoxylate ester.
引用
收藏
页码:1533 / 1536
页数:4
相关论文
共 9 条
[2]   ASYMMETRIC INDUCTION IN DIELS-ALDER REACTIONS TO ACRYLATES DERIVED FROM CHIRAL SEC-ALCOHOLS - PRELIMINARY COMMUNICATION [J].
OPPOLZER, W ;
KURTH, M ;
REICHLIN, D ;
CHAPUIS, C ;
MOHNHAUPT, M ;
MOFFATT, F .
HELVETICA CHIMICA ACTA, 1981, 64 (08) :2802-2807
[3]   HIGH ASYMMETRIC INDUCTION IN DIELS-ALDER ADDITIONS OF CYCLOPENTADIENE TO ACRYLATES DERIVED FROM ISOBORNEOL [J].
OPPOLZER, W ;
CHAPUIS, C ;
DAO, GM ;
REICHLIN, D ;
GODEL, T .
TETRAHEDRON LETTERS, 1982, 23 (46) :4781-4784
[4]   CONFIGURATION AND CONFORMATION OF (-)-8-PHENYLMETHYL 3-AMINO-2-HYDROXY-5-METHYLHEXANOATE [J].
SOLLADIECAVALLO, A ;
KHIAR, N ;
FISCHER, J ;
DECIAN, A .
TETRAHEDRON, 1991, 47 (02) :249-258
[5]   DIASTEREOSELECTIVE REDUCTION OF AN ALPHA-KETO-ESTER DERIVED FROM (-)-8-PHENYLMENTHOL - A 4-STEP SYNTHESIS OF R-HALOSTACHINE ANALOG [J].
SOLLADIECAVALLO, A ;
BENCHEQROUN, M .
TETRAHEDRON-ASYMMETRY, 1991, 2 (11) :1165-1171
[6]   PHOTOPHYSICAL PROBES OF INTRAMOLECULAR INTERACTIONS RESPONSIBLE FOR ASYMMETRIC INDUCTION [J].
WHITESELL, JK ;
YOUNATHAN, JN ;
HURST, JR ;
FOX, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) :5499-5503
[7]   ASYMMETRIC INDUCTION - REDUCTION, NUCLEOPHILIC-ADDITION TO, AND ENE REACTIONS OF CHIRAL ALPHA-KETOESTERS [J].
WHITESELL, JK ;
DEYO, D ;
BHATTACHARYA, A .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (15) :802-802
[8]   AUXILIARY STRUCTURE AND ASYMMETRIC INDUCTION IN THE ENE REACTIONS OF CHIRAL GLYOXYLATES [J].
WHITESELL, JK ;
LAWRENCE, RM ;
CHEN, HH .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (25) :4779-4784
[9]   PREPARATION OF 8-PHENYLMENTHOL AND ITS DIASTEREOMER, 2-EPI,ENT-8-PHENYLMENTHOL - A CAVEAT [J].
WHITESELL, JK ;
LIU, CL ;
BUCHANAN, CM ;
CHEN, HH ;
MINTON, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (04) :551-553