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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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 and Nicholas J. Turro

Volume 6, Issue 5, 2009

Page: [362 - 366] Pages: 5

DOI: 10.2174/157017809788681400

Price: $65

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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