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

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

Volume: 6 Issue: 5

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

Affiliation:

Keywords: Peterson reaction, diastereoselectivity, asymmetric synthesis, singlet oxygen

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.

Cite this article as:

Solomon R. Marissa, Saito Hideaki, Sivaguru J., Jockusch Steffen, Inoue Yoshihisa, Adam Waldemar and Turro J. Nicholas, Isolation and syn Elimination of a Peterson Adduct to Obtain Optically Pure Product in the Diastereoselective Synthesis of Oxazolidinone- Functionalized Enecarbamates, Letters in Organic Chemistry 2009; 6 (5) . https://dx.doi.org/10.2174/157017809788681400