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Updated: Jan 25, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Michael Addition of P-Nucleophiles to Conjugated Nitrosoalkenes
Yana A Naumovich1, Sema L Ioffe1, Alexey Yu Sukhorukov1,2,3
1N. D. Zelinsky Institute of Organic Chemistry , Leninsky Prospect, 47 , Moscow 119991 , Russia.
Abstract:
A general approach to various α-phosphorus-substituted oximes (β-oximinoalkyl-substituted phosphonates, phosphine oxides, phosphine-borane complexes, and phosphonium salts) was developed. The strategy exploits hitherto unknown Michael addition of PH-containing compounds (diphenylphosphine oxide, diisopropyl phosphite, phosphine-borane complexes, and triphenylphosphonium bromide) to unstable conjugated nitrosoalkenes, which are generated in situ from corresponding nitrosoacetals. The resulting α-phosphorus-substituted oximes can be considered as useful P-, N-, and O-ligands for catalysis and precursors to valuable β-aminophosphonates.
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