Synthesis of Chiral α-(N-Sulfoximido) Phosphines, Phosphine Oxides, and Phosphonates through Hydrophosphination and Hydrophosphorylation of N-Vinyl Sulfoximines

摘要

The reaction of N-vinyl sulfoximines with HPPh2, HP(O)Ph2, and HP(O)(OMe)2 gave the corresponding α-(N-sulfoximido) phosphines, phosphine oxides, and phosphonates, respectively, with high regioselectivity in high yield. The N-vinyl sulfoximines showed an enamine-like regioselectivity in hydrophosphination and hydrophosphorylation (Pudovik reaction). While the acid-catalyzed hydrolysis of a cyclic N-vinyl sulfoximine gave the corresponding NH-sulfoximine and cyclohexanone, its hydro-boration/oxidation afforded the corresponding N-(β-hydroxycyclohexenyl) sulfoximine. The structure of an α-(N-sulfoximido) phosphine was determined by X-ray crystal structure analysis.