Journal of Organic Chemistry p. 7244 - 7254 (2019)
Update date:2022-08-03
Topics:
Naumovich, Yana A.
Ioffe, Sema L.
Sukhorukov, Alexey Yu.
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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