1377584-94-5Relevant articles and documents
Functionalization of α-hydroxyphosphonates as a convenient route to: N -tosyl-α-aminophosphonates
Cytlak, Tomasz,Skibińska, Monika,Kaczmarek, Patrycja,Ka?mierczak, Marcin,Rapp, Magdalena,Kubicki, Maciej,Koroniak, Henryk
, p. 11957 - 11974 (2018)
Direct conversion of the α-hydroxyl group by para-toluenesulfonamide to yield α-(N-tosyl)aminophosphonates is reported. α-Aminophosphonates 23a,b-37a,b were obtained from the corresponding α-hydroxyphosphonates 6a,b-21a,b in the presence of K2CO3, via the retro-Abramov reaction of the appropriate aldehydes, 1-5. The subsequent formation of imines with simultaneous addition of diethyl phosphite provided access to the α-sulfonamide phosphonates 23a,b-37a,b with better diastereoselectivity than in the case of the Pudovik reaction. The mechanism for this transformation is proposed herein. When Cbz N-protected aziridine 9a,b and phenylalanine analogue 12a,b were exploited, intramolecular substitution was observed, leading to the corresponding epoxide 38 as the sole product, or oxazolidin-2-one 39 as a minor product. Analogous substitution was not observed in the case of proline 18a,b and serine 21a,b derivatives.
