RUS  ENG
Full version
JOURNALS // Mendeleev Communications // Archive

Mendeleev Commun., 2021 Volume 31, Issue 5, Pages 686–689 (Mi mendc1023)

This article is cited in 1 paper

Communications

Stereoselective approach to conjugated enone oximes from aliphatic nitro compounds and sulfur ylides

R. T. Akhmirovab, S. L. Ioffea, A. Yu. Sukhorukova

a N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
b D.Mendeleev University of Chemical Technology of Russia, Moscow, Russian Federation

Abstract: A novel approach to conjugated enone oximes from aliphatic nitro compounds deals with double silylation of N,N-bis(silyloxy) enamines followed by a stereoselective reaction with an ester-stabilized sulfur ylide. The proposed mechanism involves the generation of labile nitrosoalkenes as intermediates, which react with the sulfur ylide to give target enone oximes.

Keywords: ylides, unsaturated oximes, nitro compounds, nitrosoalkenes, Michael addition.

Language: English

DOI: 10.1016/j.mencom.2021.09.031



© Steklov Math. Inst. of RAS, 2025