Synlett 2002(8): 1344-1346
DOI: 10.1055/s-2002-32988
LETTER
© Georg Thieme Verlag Stuttgart · New York

TBAT-Mediated Nitrone Formation of ω-Mesyloxy-O-tert-butyldiphenylsilyl-oximes: Facile Synthesis of Cyclic Nitrones from Hemiacetals

Osamu Tamura*, Atsushi Toyao, Hiroyuki Ishibashi*
Faculty of Pharmaceutical Sciences, Kanazawa University, Takara-machi, Kanazawa, Ishikawa 920-0934, Japan
e-Mail: tamura@mail.p.kanazawa-u.ac.jp;
Further Information

Publication History

Received 22 May 2002
Publication Date:
25 July 2002 (online)

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Abstract

Chiral and cyclic nitrones were synthesized by TBAT-mediated desilylative cyclization of ω-mesyloxy-O-tert-butyldiphenylsilyloximes, readily prepared from sugar derivatives by a consecutive treatment with O-tert-butyldiphenylsilylhydroxyl­amine and with mesyl chloride. The method was applied to sequential nitrone formation and intramolecular cycloaddition.