Asymmetric Baylis-Hillman reactions using (R)-4-(3-hydroxy-4,4-dimethyl-2-oxopyrrolidin-1-yl) benzoic acid acrylate derivatives in solution and on solid support

被引：10

作者：

Calmès, M

Akkari, R

Barthes, N

Escale, F

Martinez, J

机构：

[1] Univ Montpellier I, UMR CNRS 5810, Lab Aminoacides Peptides & Prot, F-34095 Montpellier, France

[2] Univ Montpellier 2, UMR CNRS 5810, Lab Aminoacides Peptides & Prot, F-34095 Montpellier, France

来源：

TETRAHEDRON-ASYMMETRY | 2005年 / 16卷 / 12期

关键词：

D O I：

10.1016/j.tetasy.2005.05.016

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The influence of several variables on the course of the Baylis-Hillman reaction between the (R)-4-(3-hydroxy-4,4dimethyl-2-oxopyrrolidin-1-yl) benzoic acid acrylate derivatives (R)-2 and (R)-3 and aromatic aldehydes has been investigated both in solution and on solid support: these resulted in comparable results with the formation or adducts in high yield and moderate selectivity. (c) 2005 Elsevier Ltd. All rights reserved.

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页码：2179 / 2185

页数：7

相关论文

共 36 条

[1] Metal- and ligand-accelerated catalysis of the Baylis-Hillman reaction [J].

Aggarwal, VK ;

Mereu, A ;

Tarver, GJ ;

McCague, R .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21) :7183-7189

[2]

Akiyama H, 2001, EUR J ORG CHEM, V2001, P2265, DOI 10.1002/1099-0690(200106)2001:12<2265::AID-EJOC2265>3.0.CO

[3]

2-8

[4] (R)- or (S)-4-(3-hydroxy-4,4-dimethyl-2-oxopyrrolidin-1-yl)benzoic acid as a new chiral auxiliary for solid phase asymmetric Diels-Alder reactions [J].

Akkari, R ;

Calmès, M ;

Escale, F ;

Iapichella, J ;

Rolland, M ;

Martinez, J .

TETRAHEDRON-ASYMMETRY, 2004, 15 (16) :2515-2525

[5] (S)-(3-hydroxy-4,4-dimethyl-2-oxopyrrolidin-1-yl) acetic acid as a solid supported chiral auxiliary in the asymmetric synthesis of β2-homoarylglycines [J].

Akkari, R ;

Calmès, M ;

Di Malta, D ;

Escale, FO ;

Martinez, J .

TETRAHEDRON-ASYMMETRY, 2003, 14 (09) :1223-1228

[6] Toward Diels-Alder reactions on a solid support using polymer bound N-substituted 3-hydroxy-4,4-dimethyl-2-pyrrolidinone acrylate derivatives [J].

Akkari, R ;

Calmès, M ;

Martinez, J .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (11) :2441-2450

[7] Synthesis of a new insoluble polymer-supported chiral alcohol auxiliary and its first application to nucleophilic addition to ketenes [J].

Akkari, R ;

Calmes, M ;

Mai, N ;

Rolland, M ;

Martinez, J .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (17) :5859-5865

[8] 1,3-DIPOLAR CYCLOADDITIONS TO BAYLIS-HILLMAN ADDUCTS - RATIONALE FOR THE OBSERVED DIASTEREOSELECTIVITY [J].

ANNUNZIATA, R ;

BENAGLIA, M ;

CINQUINI, M ;

COZZI, F ;

RAIMONDI, L .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (15) :4697-4706

[9] Applications of Baylis-Hillman acetates:: one-pot, facile and convenient synthesis of substituted γ-lactams [J].

Basavaiah, D ;

Rao, JS .

TETRAHEDRON LETTERS, 2004, 45 (08) :1621-1625

[10] The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction [J].

Basavaiah, D ;

Rao, PD ;

Hyma, RS .

TETRAHEDRON, 1996, 52 (24) :8001-8062

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