The Peterson reaction of (4R)-N-(trimethylsilyl)methyl-4-alkyloxazolidin-2-one gives (E/Z)-(4R)-N-(2,3- diphenylbut-1-enyl)-4-alkyloxazolidin-2-ones (enecarbamates) with increasing (Z)-selectivity and moderate-to-high diastereoselectivity in the individual E isomer as a function of increasing temperature. X-ray structure of the Peterson adduct, (4R,3S)-N-(2,3-diphenyl-2-hydroxy-but-1-enyl)-4-alkyloxazolidin-2-one (enecarbamates), reveals the rationale for the formation of a single isomer through syn elimination. The optically pure enecarbamates obtained with the Peterson adduct were further employed for photochemical and photophysical studies.
Keywords: Peterson reaction, diastereoselectivity, asymmetric synthesis, singlet oxygen
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