Isolation and syn Elimination of a Peterson Adduct to Obtain Optically Pure Product in the Diastereoselective Synthesis of Oxazolidinone- Functionalized Enecarbamates

Author(s): Marissa R. Solomon, Hideaki Saito, J. Sivaguru, Steffen Jockusch, Yoshihisa Inoue, Waldemar Adam, Nicholas J. Turro.

Journal Name: Letters in Organic Chemistry

Volume 6 , Issue 5 , 2009

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Abstract:

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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Article Details

VOLUME: 6
ISSUE: 5
Year: 2009
Page: [362 - 366]
Pages: 5
DOI: 10.2174/157017809788681400
Price: $58