Scandium trifluoromethanesulfonate-catalyzed chemoselective allylation reactions of carbonyl compounds with tetraallylgermane in aqueous media

被引：42

作者：

Akiyama, T

Iwai, J

机构：

[1] Department of Chemistry, Faculty of Sciences, Gakushuin University, Toshima, Tokyo, 1-5-1, Mejiro

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 05期

关键词：

D O I：

10.1016/S0040-4039(96)02466-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Scandium(III) triflate-catalyzed allylation of carbonyl compounds with tetraallylgermane proceeded readily in aqueous nitromethane to afford homoallyl alcohols in excellent to good yields. The presence of H2O is indispensable for the allylation of aldehydes to proceed smoothly. Aldehydes were allylated exclusively in the presence of ketone moieties. (C) 1997, Elsevier Science Ltd.

引用

页码：853 / 856

页数：4

共 32 条

[1] Scandium trifluoromethanesulfonate, a novel catalyst for the addition of allyltrimethylsilane to aldehydes.
Aggarwal, VK
Vennall, GP
[J]. TETRAHEDRON LETTERS, 1996, 37 (21) : 3745 - 3746
[2] YTTERBIUM TRIFLUOROMETHANESULFONATE [YB(OTF)(3)] AS A NOVEL CATALYST FOR THE ALLYLATION OF ALDEHYDES
ASPINALL, HC
BROWNING, AF
GREEVES, N
RAVENSCROFT, P
[J]. TETRAHEDRON LETTERS, 1994, 35 (26) : 4639 - 4640
[3] BARNES JM, 1968, ORGANOMET CHEM REV A, V3, P137
[4] The solvent promoted addition of tetraallyltin to aldehydes: A convenient and chemoselective allylation procedure
Cokley, TM
Marshall, RL
McCluskey, A
Young, DJ
[J]. TETRAHEDRON LETTERS, 1996, 37 (11) : 1905 - 1908
[5] ON THE STEREOSELECTIVE OPENING OF CHIRAL DIOXANE ACETALS - NUCLEOPHILE DEPENDENCE
DENMARK, SE
ALMSTEAD, NG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (23) : 6485 - 6487
[6] Fleming I., 1991, Comprehensive Organic Synthesis, V2, P563
[7] Fleming I., 1989, ORG REACTIONS, V37, P57
[8] AQUEOUS REACTIONS WITH A LEWIS-ACID AND AN ORGANOMETALLIC REAGENT - THE SCANDIUM TRIFLUOROMETHANESULFONATE-CATALYZED ALLYLATION REACTION OF CARBONYL-COMPOUNDS WITH TETRAALLYLTIN
HACHIYA, I
KOBAYASHI, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (25) : 6958 - 6960
[9] ALLYLATION OF CARBONYL-COMPOUNDS MEDIATED BY GERMANIUM(II) IODIDE
HASHIMOTO, Y
KAGOSHIMA, H
SAIGO, K
[J]. TETRAHEDRON LETTERS, 1994, 35 (27) : 4805 - 4808
[10] CATALYTIC ASYMMETRIC ALLYLATION OF ALDEHYDES
KECK, GE
TARBET, KH
GERACI, LS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (18) : 8467 - 8468

← 1 2 3 4 →