Toward the development of a general chiral auxiliary .5. High diastereofacial selectivity in cycloadditions with trienol silyl ethers: An application to an enantioselective synthesis of (-)-cassioside

被引:32
作者
Boeckman, RK
Liu, YG
机构
[1] Department of Chemistry, University of Rochester, Rochester
关键词
D O I
10.1021/jo961613q
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[No abstract available]
引用
收藏
页码:7984 / 7985
页数:2
相关论文
共 22 条
[1]   AN APPROACH TO PSEUDOMONIC ACIDS FROM ACETYLENIC PRECURSORS - SYNTHESIS OF 2-(HYDROXYMETHYL)-3-BUTYN-1-OL [J].
BATES, HA ;
FARINA, J ;
TONG, M .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (14) :2637-2641
[2]   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
[3]   TOWARD THE DEVELOPMENT OF A GENERAL CHIRAL AUXILIARY .2. EVALUATION OF CAMPHOR LACTAM IMIDE AUXILIARIES FOR ASYMMETRIC ALDOL REACTIONS [J].
BOECKMAN, RK ;
JOHNSON, AT ;
MUSSELMAN, RA .
TETRAHEDRON LETTERS, 1994, 35 (46) :8521-8524
[4]   TOWARD THE DEVELOPMENT OF A GENERAL CHIRAL AUXILIARY .3. DESIGN AND EVALUATION OF A NOVEL CHIRAL BICYCLIC LACTAM FOR ASYMMETRIC ALDOL CONDENSATIONS - EVIDENCE FOR THE IMPORTANCE OF DIPOLE ALIGNMENT IN THE TRANSITION-STATE [J].
BOECKMAN, RK ;
CONNELL, BT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (49) :12368-12369
[5]  
BOECKMAN RK, 1996, UNPUB J ORG CHEM, V61
[6]   THE PARA-METHOXYBENZYL GROUP AS PROTECTIVE GROUP OF THE ANOMERIC CENTER - SELECTIVE CONVERSIONS OF HYDROXY-GROUPS INTO BROMO GROUPS IN PARA-METHOXYBENZYL 2-DEOXY-2-PHTHALIMIDO-BETA-D-GLUCOPYRANOSIDE [J].
CLASSON, B ;
GAREGG, PJ ;
SAMUELSSON, B .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1984, 38 (05) :419-422
[7]   DEMONSTRATION OF THE SYNTHETIC POWER OF OXAZABOROLIDINE-CATALYZED ENANTIOSELECTIVE DIELS-ALDER REACTIONS BY VERY EFFICIENT ROUTES TO CASSIOL AND GIBBERELLIC-ACID [J].
COREY, EJ ;
GUZMANPEREZ, A ;
LOH, TP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (08) :3611-3612
[8]  
Ferrier R.J., 1980, METHODS CARBOHYDR CH, V8, P251
[9]  
FUJIWARA A, 1962, B CHEM SOC JPN, V35, P2042
[10]   SYNTHESIS OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS BY PALLADIUM(II)-CATALYZED DEHYDROSILYLATION OF SILYL ENOL ETHERS [J].
ITO, Y ;
HIRAO, T ;
SAEGUSA, T .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (05) :1011-1013