Phosphine catalyzed aldol reaction between ketene silyl acetals and aldehydes: nucleophilic O-Si and C-Si bond cleavage by phosphines

被引：61

作者：

Matsukawa, S ^{[1
]}

Okano, N ^{[1
]}

Imamoto, T ^{[1
]}

机构：

[1] Chiba Univ, Fac Sci, Dept Chem, Inage Ku, Chiba 2638522, Japan

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 01期

关键词：

phosphines; aldol reactions; naked enolates;

D O I：

10.1016/S0040-4039(99)02014-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly nucleophilic phosphine, tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP), catalyzes the aldol reaction between ketene silyl acetals and aldehydes to give the corresponding aldol products in good to high yields. This reaction is considered to proceed through naked enolates produced by nucleophilic O-Si and C-Si bond cleavage. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：103 / 107

页数：5

共 32 条

[1] [Anonymous], [No title captured]
[2] Asymmetric formation of quaternary carbon centers catalyzed by novel chiral 2,5-dialkyl-7-phenyl-7-phosphabicyclo[2.2.1]heptanes
Chen, ZG
Zhu, GX
Jiang, QZ
Xiao, DM
Cao, P
Zhang, X
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (16) : 5631 - 5635
[3] ACTIVATION OF SILICON HYDROGEN, SILICON OXYGEN, SILICON NITROGEN BONDS IN HETEROGENEOUS PHASE - SOME NEW METHODS IN ORGANIC-SYNTHESIS
CORRIU, RJP
PERZ, R
REYE, C
[J]. TETRAHEDRON, 1983, 39 (06) : 999 - 1009
[4] CREGER PL, 1972, TETRAHEDRON LETT, P79
[5] Lewis base-catalyzed, asymmetric aldol additions of methyl ketone enolates
Denmark, SE
Stavenger, RA
Wong, KT
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (04) : 918 - 919
[6] Dubois J. E., 1968, J CHEM SOC CHEM COMM, P1567
[7] Evans D. A., 1982, TOP STEREOCHEM, V13, P1, DOI DOI 10.1002/9780470147221.CHL
[8] Heathcock C. H., 1984, ASYMMETRIC SYNTHESIS, V3, P111
[9] KIM BM, 1991, COMPREHENSIVE ORGANI, V2, P325
[10] CHEMISTRY OF O-SILYLATED KETENE ACETALS - STEREOCONTROLLED SYNTHESIS OF 2-DEOXY-ERYTHRO-PENTOSES AND 2-DEOXY-2-C-ALKYL-ERYTHRO-PENTOSES
KITA, Y
TAMURA, O
ITOH, F
YASUDA, H
KISHINO, H
KE, YY
TAMURA, Y
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (03) : 554 - 561

← 1 2 3 4 →