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.
Citation:
R. T. Akhmirov, S. L. Ioffe, A. Yu. Sukhorukov, “Stereoselective approach to conjugated enone oximes from aliphatic nitro compounds and sulfur ylides”, Mendeleev Commun., 31:5 (2021), 686–689
Linking options:
https://www.mathnet.ru/eng/mendc1023
https://www.mathnet.ru/eng/mendc/v31/i5/p686
This publication is cited in the following 1 articles:
Pavel Yu. Ushakov, Sema L. Ioffe, Alexey Yu. Sukhorukov, “Recent advances in the application of ylide-like species in [4 + 1]-annulation reactions: an updated review”, Org. Chem. Front., 9:19 (2022), 5358