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

被引：22

作者：

Akiyama, T ^{[1
]}

Iwai, J ^{[1
]}

Sugano, M ^{[1
]}

机构：

[1] Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan

来源：

TETRAHEDRON | 1999年 / 55卷 / 24期

关键词：

allylation; germanium and compounds; scandium and compounds; solvents and solvent effects;

D O I：

10.1016/S0040-4020(99)00371-3

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 highly chemoselectively in the presence of ketone moieties. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：7499 / 7508

页数：10

共 86 条

[51] New methodologies for the synthesis of compound libraries
Kobayashi, S
[J]. CHEMICAL SOCIETY REVIEWS, 1999, 28 (01) : 1 - 15
[52] KOBAYASHI S, 1993, SYNLETT, P472
[53] REPEATED USE OF THE CATALYST IN LN(OTF)3-CATALYZED ALDOL AND ALLYLATION REACTIONS
KOBAYASHI, S
HACHIYA, I
YAMANOI, Y
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1994, 67 (08) : 2342 - 2344
[54] KORSHAK VV, 1957, DOKL AKAD NAUK SSSR+, V112, P436
[55] Li C. -J., 1997, ORGANIC REACTIONS AQ
[56] ORGANIC-REACTIONS IN AQUEOUS-MEDIA - WITH A FOCUS ON CARBON-CARBON BOND FORMATION
LI, CJ
[J]. CHEMICAL REVIEWS, 1993, 93 (06) : 2023 - 2035
[57] Majetich G., 1989, Organic Synthesis: Theory and Application, V1, P173
[58] SCALES OF NUCLEOPHILICITY AND ELECTROPHILICITY - A SYSTEM FOR ORDERING POLAR ORGANIC AND ORGANOMETALLIC REACTIONS
MAYR, H
PATZ, M
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (09): : 938 - 957
[59] PIG-LIVER ESTERASE CATALYZED HYDROLYZES OF RACEMIC ALPHA-SUBSTITUTED ALPHA-HYDROXY ESTERS
MOORLAG, H
KELLOGG, RM
KLOOSTERMAN, M
KAPTEIN, B
KAMPHUIS, J
SCHOEMAKER, HE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (23) : 5878 - 5881
[60] Chiral bis(oxazolinyl)phenylrhodium(III) complexes as Lewis acid catalysts for enantioselective allylation of aldehydes
Motoyama, Y
Narusawa, H
Nishiyama, H
[J]. CHEMICAL COMMUNICATIONS, 1999, (02) : 131 - 132

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