Control of the mode selectivity (ene reaction versus [2 + 2] cycloaddition) in the photooxygenation of ene carbamates: directing effect of an alkenylic nitrogen functionality |
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| Authors: | Adam Waldemar Bosio Sara G Turro Nicholas J |
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| Institution: | Institut für Organische Chemie, Universit?t Würzburg, Am Hubland, D-97074 Würzburg, Germany. adam@chemie.uni-wuerzburg.de |
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| 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. |
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