Functionalization of α-hydroxyphosphonates as a convenient route to N-tosyl-α-aminophosphonates.

ABSTRACT: 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 ep

SUBMITTER: Cytlak T 

PROVIDER: S-EPMC9079259 | biostudies-literature | 2018 Mar

REPOSITORIES: biostudies-literature