Complete control of regioselectivity in the intramolecular [2+2] photocycloaddition of 2-alkenyl-3(2H)-furanones by the Length of the side chain

被引：18

作者：

Bach, T ^{[1
]}

Kemmler, M

Herdtweck, E

机构：

[1] Tech Univ Munich, Lehrstuhl Organ Chem 1, D-85747 Garching, Germany

[2] Tech Univ Munich, Lehrstuhl Anorgan Chem, D-85747 Garching, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 05期

关键词：

D O I：

10.1021/jo0264372

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 2-(omega-alkenyl)-substituted 2-methyl-3(2H)-furanones 2a and 2b were prepared from biacetyl (3) in four reaction steps and in overall yields of 20% and 21%, respectively. They underwent a clean intramolecular [2 + 2] photocycloaddition upon irradiation at lambda = 350 nm. Whereas compound 2a reacted in the expected manner and yielded 7-oxabicyclo[3.2.1.0(3,6)]octane 7 (87% yield), the regioselectivity in the photocycloaddition of compound 2b was completely reversed. The reaction led to compound 8 (92% yield) with the unusual 9-oxabicyclo[4.2.1.0(3,8)]nonane skeleton, the structure of which was established by single-crystal X-ray crystallography.

引用

页码：1994 / 1997

页数：4

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