An Asymmetric Tandem Conjugative Addition-Intramolecular Cyclisation Process to Provide Functionalised 3,6-Dihydropyrans and 4,5-Epoxytetrahydropyrans

被引：24

作者：

Catalan-Munoz, Silvia ^{[1
]}

Mueller, Constanze A. ^{[1
]}

Ley, Steven V. ^{[1
]}

机构：

[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 01期

基金：

瑞士国家科学基金会;

关键词：

Epoxidation; Organocatalysis; Aldol reactions; Wittig reactions; RING-CLOSING METATHESIS; VINYL SULFONIUM SALTS; DIELS-ALDER REACTIONS; ORGANOCATALYTIC ROUTE; PHOSPHORUS COMPOUNDS; ENANTIOSELECTIVE SYNTHESIS; CHIRAL 1,2-OXAZINES; GENERAL SYNTHESIS; FACILE SYNTHESIS; WITTIG REACTION;

D O I：

10.1002/ejoc.200901145

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of 3,6-dihydropyrans and 4,5-epoxytetrahydropyrans starting from enantiomerically pure beta-hydroxy aldehyde (prepared by an organocatalytic aldol reaction) is described. The key step is a tandem sequence, which consists of a base-promoted conjugative addition to a vinyl on-ium salt, followed by either an intramolecular Wittig process to provide 3,6-dihydropyran derivatives or an intramolecular cyclisation/epoxidation process to afford 4,5-epoxytetrahydropyran scaffolds, The products obtained by this method are common substructures in polyketide natural products.

引用

页码：183 / 190

页数：8

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