VERSATILE SYNTHESIS OF ALICYCLIC AND ACYCLIC COMPOUNDS WITH ALTERNATE AND REMOTE C-METHYL SUBSTITUTION PATTERNS VIA ASYMMETRIC SEQUENTIAL OLEFINATION AND ENE REACTIONS

被引:36
作者
HANESSIAN, S
BEAUDOIN, S
机构
[1] Department of Chemistry, Station A, Montréal, Que. H3C 3J7
关键词
D O I
10.1016/0040-4039(93)88009-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of enantiomerically pure alkyl cyclohexane ethylidene derivatives with 2,3-di-O-benzyl D- and L-glyceraldehyde and related aldehydes in the presence of Lewis acids leads to enantiomerically pure or enriched branched alkylcyclohexenes. These can be oxidized to acyclic motifs with a predetermined C-methyl substitution pattern.
引用
收藏
页码:7659 / 7662
页数:4
相关论文
共 26 条
[1]   SYNTHESIS AND ANTIHERPETIC ACTIVITY OF (S)-9-[2,3-DIHYDROXY-1-PROPOXY)METHYL]GUANINE, (R)-9-[2,3-DIHYDROXY-1-PROPOXY)METHYL]GUANINE, AND (+/-)-9-[(2,3-DIHYDROXY-1-PROPOXY)METHYL]GUANINE, LINEAR ISOMERS OF 2'-NOR-2'-DEOXYGUANOSINE [J].
ASHTON, WT ;
CANNING, LF ;
REYNOLDS, GF ;
TOLMAN, RL ;
KARKAS, JD ;
LIOU, R ;
DAVIES, MEM ;
DEWITT, CM ;
PERRY, HC ;
FIELD, AK .
JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (07) :926-933
[2]   ISOMERS OF DICHLOROBIS(L-CYCLOHEXANEDIAMINE)COBALT(3) ION [J].
ASPERGER, RG ;
LIU, CF .
INORGANIC CHEMISTRY, 1965, 4 (10) :1492-&
[3]  
BEAUDOIN S, 1992, THESIS U MONTREAL
[4]  
Bu'Lock J. D., 1979, COMPREHENSIVE ORGANI, V5, P927
[5]   SYNTHESES OF CHIRAL CYCLOHEXYLIDENEPROPENES AND CYCLOHEXYLIDENEACETALDEHYDES [J].
DURAISAMY, M ;
WALBORSKY, HM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (10) :3252-3264
[6]   STEREOSELECTIVE ORGANIC-REACTIONS - CATALYSTS FOR CARBONYL ADDITION PROCESSES [J].
EVANS, DA .
SCIENCE, 1988, 240 (4851) :420-426
[7]   DIASTEREOSELECTIVE ALDOL REACTIONS USING BETA-KETO IMIDE DERIVED ENOLATES - A VERSATILE APPROACH TO THE ASSEMBLAGE OF POLYPROPIONATE SYSTEMS [J].
EVANS, DA ;
CLARK, JS ;
METTERNICH, R ;
NOVACK, VJ ;
SHEPPARD, GS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (02) :866-868
[8]   PREPARATION, SEPARATION, AND CHARACTERIZATION OF LEL3-ISOMERS AND OB3-ISOMERS OF TRIS(TRANS-1,2-CYCLOHEXANEDIAMINE) RHODIUM (III) COMPLEXES [J].
GALSBOL, F ;
STEENBOL, P ;
SORENSEN, BS .
ACTA CHEMICA SCANDINAVICA, 1972, 26 (09) :3605-3611
[9]   DESIGN AND REACTIVITY OF TOPOLOGICALLY UNIQUE, CHIRAL PHOSPHONAMIDES - REMARKABLE DIASTEREOFACIAL SELECTIVITY IN ASYMMETRIC OLEFINATION AND ALKYLATION [J].
HANESSIAN, S ;
DELORME, D ;
BEAUDOIN, S ;
LEBLANC, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (19) :5754-5756
[10]   VERSATILE SYNTHESIS OF ALICYCLIC AND ACYCLIC COMPOUNDS WITH ALTERNATE AND REMOTE C-METHYL SUBSTITUTION PATTERNS VIA ASYMMETRIC SEQUENTIAL OLEFINATION AND ENE REACTIONS [J].
HANESSIAN, S ;
BEAUDOIN, S .
TETRAHEDRON LETTERS, 1992, 33 (50) :7659-7662