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
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作者:
ADAM, W
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机构:Institute of Organic Chemistry, University of Würzbug, W-8700 Würzburg, Am Hubland
ADAM, W
BRUNKER, HG
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机构:Institute of Organic Chemistry, University of Würzbug, W-8700 Würzburg, Am Hubland
BRUNKER, HG
NESTLER, B
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机构:Institute of Organic Chemistry, University of Würzbug, W-8700 Würzburg, Am Hubland
NESTLER, B
机构:
[1] Institute of Organic Chemistry, University of Würzbug, W-8700 Würzburg, Am Hubland
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.