Planar chiral PHANOLs as organocatalysts for the Diels-Alder reaction via double hydrogen-bonding to a carbonyl group

被引：34

作者：

Braddock, DC

MacGilp, ID

Perry, BG

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

[2] GlaxoSmithKline Ltd, Tonbridge TN11 9AN, Kent, England

来源：

SYNLETT | 2003年 / 08期

关键词：

organocatalysis; planar chiral bisphenols; double hydrogen bonding; Diels-Alder reactions; carbonyl activation;

D O I：

10.1055/s-2003-39890

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Planar chiral PHANOLs have been shown to catalyze Diels-Alder reactions of alpha,beta-unsaturated aldehydes and ketones with various dienes. Rate accelerations of up to ca. 30-fold were obtained using the electron deficient 4,12-dihydroxy-7,15-dinitro[2.2]paracyclophane as a catalyst. It is proposed that the carbonyl group of the dienophile is activated via a double hydrogen-bonding mode. Although the PHANOLs are inherently chiral, little or no asymmetric induction was observed when using enantiopure (R)-PHANOL.

引用

页码：1121 / 1124

页数：4

共 20 条

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