FACILE AND HIGHLY STEREOSELECTIVE ALLYLATION OF ALDEHYDES USING ALLYLTRICHLOROSILANES IN DMF

被引:128
作者
KOBAYASHI, S
NISHIO, K
机构
[1] Department of Applied Chemistry, Faculty of Science, Science University of Tokyo (SUT), Shinjuku-ku, Tokyo, 162, Kagurazaka
关键词
D O I
10.1016/S0040-4039(00)79181-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Allyltrichlorosilanes regioselectively react with aldehydes in N,N-dimethylformamide (DMF) without catalyst to afford the corresponding homoallylic alcohols in high yields. Syn and anti homoallylic alcohols are stereoselectively obtained from (Z)- and (E)-crotyltrichlorosilane, respectively, under neutral conditions.
引用
收藏
页码:3453 / 3456
页数:4
相关论文
共 13 条
[1]  
Fleming I., 1989, ORG REACTIONS, V37, P57
[2]   STEREOCHEMISTRY AND MECHANISM OF ASYMMETRIC ALLYLATION OF ALDEHYDES WITH OPTICALLY-ACTIVE ALLYLSILICONATES [J].
HAYASHI, T ;
MATSUMOTO, Y ;
KIYOI, T ;
ITO, Y ;
KOHRA, S ;
TOMINAGA, Y ;
HOSOMI, A .
TETRAHEDRON LETTERS, 1988, 29 (44) :5667-5670
[3]   CHROMIUM(II) MEDIATED THREO SELECTIVE SYNTHESIS OF HOMOALLYL ALCOHOLS [J].
HIYAMA, T ;
KIMURA, K ;
NOZAKI, H .
TETRAHEDRON LETTERS, 1981, 22 (11) :1037-1040
[4]   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
[5]  
HOSOMI A, 1976, TETRAHEDRON LETT, P1295
[6]   PENTACO-ORDINATE SILICON-COMPOUNDS IN SYNTHESIS - REGIOSPECIFIC ALLYLATION OF ALDEHYDES BY USE OF TRIETHYLAMMONIUM BIS(PYROCATECHOLATO)ALLYLSILICATES [J].
HOSOMI, A ;
KOHRA, S ;
TOMINAGA, Y .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (20) :1517-1518
[7]   CHEMISTRY OF ORGANO-SILICON COMPOUNDS .240. PENTACOORDINATE ALLYLSILICATES - CHARACTERIZATION AND HIGHLY STEREOSELECTIVE REACTION WITH ALDEHYDES [J].
KIRA, M ;
SATO, K ;
SAKURAI, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (14) :4599-4602
[8]   CHEMISTRY OF ORGANOSILICON COMPOUNDS .234. REGIOSPECIFIC AND HIGHLY STEREOSELECTIVE ALLYLATION OF ALDEHYDES WITH ALLYLTRIFLUOROSILANE ACTIVATED BY FLUORIDE IONS [J].
KIRA, M ;
KOBAYASHI, M ;
SAKURAI, H .
TETRAHEDRON LETTERS, 1987, 28 (35) :4081-4084
[9]   CHEMISTRY OF ORGANO-SILICON COMPOUNDS .254. STEREOHOMOGENEOUS SYNTHESIS OF (E)-CROTYLTRIFLUOROSILANES AND (Z)-CROTYLTRIFLUOROSILANES AND HIGHLY STEREOSELECTIVE ALLYLATION OF ALDEHYDES [J].
KIRA, M ;
HINO, T ;
SAKURAI, H .
TETRAHEDRON LETTERS, 1989, 30 (09) :1099-1102
[10]   A FACILE SYNTHESIS OF CYANOHYDRIN TRIMETHYLSILYL ETHERS BY THE ADDITION-REACTION OF TRIMETHYLSILYL CYANIDE WITH ALDEHYDES UNDER BASIC CONDITION [J].
KOBAYASHI, S ;
TSUCHIYA, Y ;
MUKAIYAMA, T .
CHEMISTRY LETTERS, 1991, (04) :537-540