Organocatalyzed conjugate umpolung of α,β-unsaturated aldehydes for the synthesis of γ-butyrolactones

被引：658

作者：

Burstein, C ^{[1
]}

Glorius, F ^{[1
]}

机构：

[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim An Der Ruhr, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 45期

关键词：

aldehydes; carbene; heterocycles; organocatalysis; umpolung;

D O I：

10.1002/anie.200461572

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Advantage organocatalysis: N-heterocyclic carbenes can generate homoenolate equivalents under mild conditions by conjugate umpolung of α,β- unsaturated aldehydes. This organocatalytic reaction allows an efficient one-step synthesis of substituted γ-butyrolactones 1 (see scheme, Mes = mesityl).

引用

页码：6205 / 6208

页数：4

共 58 条

[31] METALATED NITROGEN DERIVATIVES OF CARBONIC-ACID IN ORGANIC-SYNTHESIS .28. THE HOMOALDOL REACTION, OR HOW TO OVERCOME PROBLEMS OF REGIO-SELECTIVITY AND STEREO-SELECTIVITY
HOPPE, D
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (12): : 932 - 948
[32] Hoppe D., 1984, ANGEW CHEM, V96, P930
[33] Johnson J. S., 2004, ANGEW CHEM, V116, P1348
[34] Catalyzed reactions of acyl anion equivalents
Johnson, JS
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (11) : 1326 - 1328
[35] Lewis base-catalyzed transformation of α,β-unsaturated aldehydes to saturated carboxylic acids, esters and amides
Kawabata, H
Hayashi, M
[J]. TETRAHEDRON LETTERS, 2002, 43 (32) : 5645 - 5647
[36] Enantioselective synthesis of quaternary stereocenters via a catalytic asymmetric Stetter reaction
Kerr, MS
Rovis, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (29) : 8876 - 8877
[37] Kerr MS, 2003, SYNLETT, P1934
[38] A highly enantioselective catalytic intramolecular Stetter reaction
Kerr, MS
de Alaniz, JR
Rovis, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (35) : 10298 - 10299
[39] Stereoselective coupling of optically active 3-trans-cinnamoyl-2-oxazolidinones with acid anhydrides by electroreduction
Kise, N
Hirata, Y
Hamaguchi, T
Ueda, N
[J]. TETRAHEDRON LETTERS, 1999, 40 (46) : 8125 - 8128
[40] INTRODUCTION OF CENTER OF CHIRALITY INTO FLUORO COMPOUNDS BY MICROBIAL TRANSFORMATION OF 2,2,2-TRIFLUOROETHANOL
KITAZUME, T
ISHIKAWA, N
[J]. CHEMISTRY LETTERS, 1984, (10) : 1815 - 1818

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