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Synthesis 2002(5): 0635-0647
DOI: 10.1055/s-2002-23539
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of β-Functionalized α,β-Unsaturated Oximes via Silylation of Nitro Compounds [1]

Vitaly M. Danilenkoa, Alexander A. Tishkov*b, Sema L. Ioffe*b, Ilya M. Lyapkaloa, Yury A. Strelenkob, Vladimir A. Tartakovskyb
a Moscow Chemical Lyceum, 4 Tamozheny proezd,109033, Moscow, Russian Federation
Fax: +7(095)3623440; e-Mail: dan@1303.ru;
b N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation
Fax: +7(095)1355328; e-Mail: tishkov@cacr.ioc.ac.ru;
Further Information

Publication History

Received 10 January 2002
Publication Date:
02 April 2002 (online)

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Abstract

A general method for the synthesis of conjugated enoximes 2 via silylation of functionalized aliphatic nitro compounds 1 has been elaborated. The configuration of obtained products has been determined by NMR spectroscopy.

Key words

nitro compounds - elimination - stereoselectivity - silylation - conjugated enoximes

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19

The formation of nitroso alkenes upon silylation of β-functionalized nitro compounds with BSA has been unambiguously proved before (see Ref. [5] ).