Thiazol-2-ylidene catalysis in intramolecular crossed aldehyde-ketone benzoin reactions

被引：66

作者：

Enders, D ^{[1
]}

Niemeier, O ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen Klinikum, Inst Organ Chem, D-52074 Aachen, Germany

来源：

SYNLETT | 2004年 / 12期

关键词：

organocatalysis; acyloins; carbenes; thiazoliurri salts; keto-aldehydes;

D O I：

10.1055/s-2004-831306

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intramolecular crossed aldehyde-ketone benzoin-type reactions catalyzed by nucleophilic carbenes, easily generated from commercially available thiazolium salts as precatalysts, are described. Five- and six-membered cyclic acyloins are obtained in moderate to good yields. Depending on the structure of the aldehyde-ketone substrate, an interchange of the alcohol and ketone function of the resulting acyloin is possible. Simple aldehyde-ketones are not good substrates due to the competing intermolecular reaction. Starting from biphenyl-2,2'-dicarbaldehyde, the intermediate acyloin is converted to 9,10-phenanthrenequinone by mild air oxidation.

引用

页码：2111 / 2114

页数：4

共 29 条

[11] Enders D., 1999, Comprehensive Asymmetric Catalysis, V3, P1093
[12] Enders D., 2002, ANGEW CHEM, V114, P1822
[13] Catalytic intramolecular crossed aldehyde-ketone benzoin reactions: A novel synthesis of functionalized preanthraquinones
Hachisu, Y
Bode, JW
Suzuki, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (28) : 8432 - 8433
[14] IDE WS, 1947, ORG REACTIONS, V4, P269
[15] Johnson J. S., 2004, ANGEW CHEM, V116, P1348
[16] Catalyzed reactions of acyl anion equivalents
Johnson, JS
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (11) : 1326 - 1328
[17] Kerr MS, 2003, SYNLETT, P1934
[18] 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
[19] Comparison of chiral thiazolium and triazolium salts as asymmetric catalysts for the benzoin condensation
Knight, RL
Leeper, FJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (12): : 1891 - 1893
[20] MAYER F, 1912, CHEM BER, V45, P1105

← 1 2 3 →