Control of the mode selectivity (ene reaction versus [2+ 2] cycloaddition) in the photooxygenation of ene carbamates: directing effect of an alkenylic nitrogen …

W Adam, SG Bosio, NJ Turro

Index: Adam, Waldemar; Bosio, Sara G.; Turro, Nicholas J. Journal of the American Chemical Society, 2002 , vol. 124, # 30 p. 8814 - 8815

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Citation Number: 34

Abstract

The geometry of the double bond in oxazolidinone-substituted ene carbamates controls the mode selectivity (ene reaction versus [2+ 2] cycloaddition) of singlet oxygen through stereoelectronic effects, whereas the chiral auxiliary provides high diastereoselectivity through steric shielding.