PHOTOOXYGENATION OF 2-ALKENYL SUBSTITUTED CHIRAL OXAZOLINES - STEREOCHEMICAL EVIDENCE FAVORING THE CIS EFFECT IN THE REGIOSELECTIVE ENE REACTION OF SINGLET OXYGEN WITH ALPHA,BETA-UNSATURATED CARBONYL DERIVATIVES

被引：27

作者：

ADAM, W

BRUNKER, HG

NESTLER, B

机构：

[1] Institute of Organic Chemistry, University of Würzbug, W-8700 Würzburg, Am Hubland

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 17期

关键词：

D O I：

10.1016/0040-4039(91)85011-S

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Photooxygenation of the title compound afforded hydroperoxides through regioselective ene reaction of singlet oxygen at the allylic position proximate to the heterocycle; the lack of diastereoselectivity in these ene reactions is taken as evidence against initial [4+2] cycloaddition of the enophile with the heterodiene.

引用

页码：1957 / 1960

页数：4

共 16 条

[1]

ADAM W, 1986, SYNTHESIS-STUTTGART, P1050

[2] SYNTHESIS OF THE 1ST ALPHA-METHYLENE-BETA-PEROXYLACTONE - REGIOSPECIFIC ENE REACTION OF O-1(2) WITH ALPHA,BETA-UNSATURATED CARBOXYLIC-ACIDS [J].