A novel synthesis of functionalized tetrahydrofurans by an oxa-Michael/Michael cyclization of γ-hydroxyenones

被引：40

作者：

Greatrex, BW

Kimber, MC

Taylor, DK ^{[1
]}

Tiekink, ERT

机构：

[1] Univ Adelaide, Dept Chem, Adelaide, SA 5004, Australia

[2] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 11期

关键词：

D O I：

10.1021/jo020700h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An approach to highly functionalized tetrahydrofuran derivatives based upon a novel Oxa-Michael/Michael dimerization of cis-gamma-hydroxyenones is presented. The reaction begins with either 1,2-dioxines or trans-gamma-hydroxyenones and proceeds by addition of one molecule of trans-gamma-hydroxyenone to another molecule of cis- or trans-gamma-hydroxyenone catalyzed by an alkoxide or hydroxide base. Subsequent intramolecular Michael addition of the keto-enolate gives the observed tetrahydrofurans. Substitution at both the 2- and 4-positions of the gamma-hydroxyenone is tolerated; however, for 4-substituted gamma-hydroxyenones, selectivity issues arise due to the possibility of heterochiral or homochiral dimerizations. The major products were those with all contiguous groups trans.

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页码：4239 / 4246

页数：8

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