A NEW STEREOSELECTIVE SYNTHESIS OF (Z)-VINYLSILANE ALLYLIC ALCOHOLS

被引:57
作者
KIM, KD [1 ]
MAGRIOTIS, PA [1 ]
机构
[1] W VIRGINIA UNIV, DEPT CHEM, MORGANTOWN, WV 26506 USA
关键词
D O I
10.1016/S0040-4039(00)97007-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new, highly stereoselective method for the synthesis of (Z)-vinylsilane allylic alcohols 3 is described. This approach to such γ-silylated allylic alcohols employs a novel 1,4-0→sp2C silyl rearrangement of appropriate silyl ether precursors 2. © 1990.
引用
收藏
页码:6137 / 6140
页数:4
相关论文
共 52 条
[11]   A NEW STEREOSPECIFIC SYNTHESIS OF TRISUBSTITUTED OLEFINS . STEREOSPECIFIC SYNTHESIS OF FARNESOL [J].
COREY, EJ ;
KATZENEL.JA ;
POSNER, GH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (16) :4245-&
[12]   THE 1,3 O-]C SILYL REARRANGEMENT OF SILYL ENOL ETHER ANIONS - SYNTHESIS OF ALPHA-SILYL KETONES [J].
COREY, EJ ;
RUCKER, C .
TETRAHEDRON LETTERS, 1984, 25 (39) :4345-4348
[13]   A PRACTICAL AND EFFICIENT SYNTHESIS OF ALPHA,BETA-UNSATURATED ACYLSILANES [J].
DANHEISER, RL ;
FINK, DM ;
OKANO, K ;
TSAI, YM ;
SZCZEPANSKI, SW .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25) :5393-5396
[14]   (E)-3-(TRIMETHYLSILYL)-2-PROPEN-1-OL - AN IMPROVED PREPARATION [J].
DENMARK, SE ;
JONES, TK .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (23) :4595-4597
[15]   REGIOSELECTION IN THE HYDROFORMYLATION OF TERT-BUTYLDIPHENYLSILYLALKENES - A NEW APPROACH TO ALDOL SYNTHESIS [J].
DOYLE, MM ;
JACKSON, WR ;
PERLMUTTER, P .
TETRAHEDRON LETTERS, 1989, 30 (02) :233-234
[16]   PHOSPHONAMIDE STABILIZED ALLYLIC CARBANIONS - NEW HOMOENOLATE ANION EQUIVALENTS [J].
EVANS, DA ;
TAKACS, JM ;
HURST, KM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (02) :371-378
[17]   REACTION OF SECONDARY AND TERTIARY ALKYLLITHIUM REAGENTS WITH VINYL DISILOXANES AND TRISILOXANES - SYNTHESIS OF ALPHA-SILYL SILANOLS [J].
FIRGO, HA ;
WEBER, WP .
ORGANOMETALLICS, 1982, 1 (04) :649-653
[18]   STUDIES ON ORGANOSILICON CHEMISTRY .100. PENTACOORDINATE ALLYLSILICONATES IN ORGANIC-SYNTHESIS - SYNTHESIS OF TRIETHYLAMMONIUM BIS(CATECHOLATO)ALLYLSILICONATES AND SELECTIVE ALLYLATION OF ALDEHYDES [J].
HOSOMI, A ;
KOHRA, S ;
OGATA, K ;
YANAGI, T ;
TOMINAGA, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (08) :2415-2420
[19]   A CHIRAL PRIMARY ALCOHOL EQUIVALENT - SILYL-ASSISTED ASYMMETRIC INDUCTION IN THE ESTER ENOLATE CLAISEN REARRANGEMENT [J].
IRELAND, RE ;
VARNEY, MD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (12) :3668-3670
[20]   CHEMISTRY OF ORGANOSILICON COMPOUNDS .259. HIGHLY STEREOSELECTIVE ALLYLATION OF ALDEHYDES WITH PENTACOORDINATE ALLYLSILICATES IN HYDROXYLIC MEDIA - DISCRIMINATION BETWEEN LINEAR AND ALPHA-BRANCHED ALKANALS [J].
KIRA, M ;
SATO, K ;
SAKURAI, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (01) :257-260