Direct organocatalytic asymmetric α-hydroxymethylation of ketones and aldehydes

被引：113

作者：

Casas, J ^{[1
]}

Sundén, H ^{[1
]}

Córdova, A ^{[1
]}

机构：

[1] Stockholm Univ, Dept Organ Chem, Arrhenius Lab, S-10691 Stockholm, Sweden

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 32期

关键词：

alpha-hydroxymethylation; organocatalysis; ketones; aldehydes; asymmetric;

D O I：

10.1016/j.tetlet.2004.06.062

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Direct organocatalytic asymmetric alpha-hydroxymethylation of ketones and aldehydes with formaldehyde has been developed, which furnished the corresponding alpha-hydroxymethylated adducts with high chemo- and enantioselectivity. The reaction is catalyzed by proline derivatives and is a simple method for the enantioselective synthesis of alpha-hydroxymethylated ketones and aldehydes, and C-2 symmetric diols. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：6117 / 6119

页数：3

共 28 条

[1] Barili PL, 1998, ENANTIOMER, V3, P357
[2] Direct catalytic asymmetric aldol reactions of aldehydes
Bogevig, A
Kumaragurubaran, N
Jorgensen, KA
[J]. CHEMICAL COMMUNICATIONS, 2002, (06) : 620 - 621
[3] Direct catalytic enantioselective α-aminoxylation of ketones:: A stereoselective synthesis of α-hydroxy and α,α′-dihydroxy ketones
Bogevig, A
Sundén, H
Córdova, A
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (09) : 1109 - 1112
[4] Direct organocatalytic aldol reactions in buffered aqueous media
Córdova, A
Notz, W
Barbas, CF
[J]. CHEMICAL COMMUNICATIONS, 2002, (24) : 3024 - 3025
[5] Direct catalytic asymmetric cross-aldol reactions in ionic liquid media
Córdova, A
[J]. TETRAHEDRON LETTERS, 2004, 45 (20) : 3949 - 3952
[6] The direct catalytic asymmetric Mannich reaction
Córdova, A
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (02) : 102 - 112
[7] One-pot organocatalytic direct asymmetric synthesis of γ-amino alcohol derivatives
Córdova, A
[J]. SYNLETT, 2003, (11) : 1651 - 1654
[8] Direct organocatalytic asymmetric Mannich-type reactions in aqueous media:: one-pot Mannich-allylation reactions
Córdova, A
Barbas, CF
[J]. TETRAHEDRON LETTERS, 2003, 44 (09) : 1923 - 1926
[9] anti-selective SMP-catalyzed direct asymmetric Mannich-type reactions:: synthesis of functionalized amino acid derivatives
Córdova, A
Barbas, CF
[J]. TETRAHEDRON LETTERS, 2002, 43 (43) : 7749 - 7752
[10] Proline-catalyzed one-step asymmetric synthesis of 5-hydroxy-(2E)-hexenal from acetaldehyde
Córdova, A
Notz, W
Barbas, CF
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (01) : 301 - 303

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