Conjugate addition of silyl groups to beta-unsubstituted enones, & Si-to-OH conversion: A synthesis of (+/-)-lavandulol

被引：14
作者：
Fleming, I
Lee, D
机构：
[1] Department of Chemistry, Cambridge CB2 1EW, Lensfield Road
来源：
TETRAHEDRON LETTERS | 1996年 / 37卷 / 38期
关键词：
D O I：
10.1016/0040-4039(96)01519-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
TMS chloride raises the yield in the conjugate addition of silylcuprates and zincates to beta-unsubstituted enones, and Si-to-OH conversion is possible using the 2-methylbut-2-enyl(diphenyl)silyl group in the presence of highly nucleophilic alkenes. Both reactions are used in a synthesis of lavandulol. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码：6929 / 6930
页数：2
相关论文
共 20 条
[11]  
FLEMING I, 1996, CHEMTRACTS ORG CHEM, V9, P1
[12]   TRIMETHYLSILYL CHLORIDE TETRAMETHYLETHYLENEDIAMINE FACILITATED ADDITIONS OF ORGANOCOPPER REAGENTS (RCU) TO ENONES [J].
JOHNSON, CR ;
MARREN, TJ .
TETRAHEDRON LETTERS, 1987, 28 (01) :27-30
[13]   The oxidation of the carbon-silicon bond [J].
Jones, GR ;
Landais, Y .
TETRAHEDRON, 1996, 52 (22) :7599-7662
[14]   NEW SYNTHETIC METHOD OF LAVANDULOLS [J].
MATSUI, M ;
KOBAYASHI, A .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1962, 26 (10) :705-&
[15]   CHLOROSILANE-ACCELERATED CONJUGATE ADDITION OF CATALYTIC AND STOICHIOMETRIC ORGANOCOPPER REAGENTS [J].
MATSUZAWA, S ;
HORIGUCHI, Y ;
NAKAMURA, E ;
KUWAJIMA, I .
TETRAHEDRON, 1989, 45 (02) :349-362
[16]  
NAKAMURA E, 1994, ORGANOCOPPER REAGENT
[17]   STEREOCHEMISTRY OF REGIOSPECIFIC HYDROSILYLATION OF ISOPRENE CATALYZED BY A PHOSPHINE-PALLADIUM COMPLEX [J].
OJIMA, I .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1977, 134 (01) :C1-C5
[18]   SILAFUNCTIONAL COMPOUNDS IN ORGANIC-SYNTHESIS .26. SILYL GROUPS SYNTHETICALLY EQUIVALENT TO THE HYDROXY GROUP [J].
TAMAO, K ;
ISHIDA, N .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1984, 269 (03) :C37-C39
[19]   SILAFUNCTIONAL COMPOUNDS IN ORGANIC-SYNTHESIS .20. HYDROGEN-PEROXIDE OXIDATION OF THE SILICON-CARBON BOND IN ORGANOALKOXYSILANES [J].
TAMAO, K ;
ISHIDA, N ;
TANAKA, T ;
KUMADA, M .
ORGANOMETALLICS, 1983, 2 (11) :1694-1696
[20]  
Tamao K., 1990, ORG SYNTH, V69, P96
12