Probing the Mode of Asymmetric Induction of Biginelli Reaction Using Proline Ester Salts

被引：34

作者：

Sohn, Jeong-Hun ^{[1
]}

Choi, Hyun-Moo ^{[2
]}

Lee, Sunjung ^{[2
]}

Joung, Seewon ^{[2
]}

Lee, Hee-Yoon ^{[2
]}

机构：

[1] Inst Pasteur Korea, Songnam 463400, South Korea

[2] Korea Adv Inst Sci & Technol, Dept Chem, Taejon 305701, South Korea

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 23期

关键词：

Asymmetric Biginelli reaction; Organocatalysis; Proline; Multicomponent reactions; MULTICOMPONENT REACTIONS; MANNICH REACTIONS; DIHYDROPYRIMIDINE SYNTHESIS; RECEPTOR ANTAGONISTS; ENAMINE CATALYSIS; AMINO-ACIDS; ORGANOCATALYSIS; MONASTROL; DERIVATIVES; INHIBITOR;

D O I：

10.1002/ejoc.200900455

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Described are the studies on the mechanism of the asymmetric Biginelli reaction using proline ester salt catalyst to explain the enantioselectivity of the 3,4-dihydropyrimidin-2(1H)-one (DHPM) formation. Of the three possible activation methods by the catalyst that could provide asymmetric induction we revealed that the steric environment of the chiral enamine formed by the condensation of beta-keto ester with the catalyst is most responsible for the enantioselectivity. This assumption is supported by experiments with the N-methylated catalyst, and the combination sets of L- or D-proline ester catalyst with racemic or chiral BINOL-derived phosphoric acid as counter acid. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

引用

页码：3858 / 3862

页数：5

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