STEREOSELECTIVE SYNTHESIS OF TETRAHYDROFURAN-3-OLS BY PHOTOCHEMICAL DELTA-HYDROGEN ABSTRACTION OF BETA-ALLYLOXY-CARBONYL COMPOUNDS

被引：3

作者：

CARLESS, HAJ

SWAN, DI

HAYWOOD, DJ

机构：

[1] Department of Chemistry, Birkbeck College, Gordon House, London, WC1H 0PP

来源：

TETRAHEDRON | 1993年 / 49卷 / 08期

关键词：

D O I：

10.1016/S0040-4020(01)80353-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

On u.v. irradiation, the unsaturated ketones and aldehydes (10) and (11) underwent intramolecular delta-hydrogen abstraction, followed by ring closure of the 1,5-biradical to give 2-alkenyltetrahydrofuran-3-ols in reasonable yields. Photocyclisation occurred with retention of geometry about the alkenyl double bond; thus, u.v. irradiation of the geranyl ketone (10a) led to the tetrahydrofuranols (12a) and (14a), whereas photolysis of the neryl ketone (11a) gave the tetrahydrofuranol isomers (13a) and (15a).

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页码：1665 / 1674

页数：10

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