Fine tuned aminal cleavage: A concise route to differentially protected enantiopure syn-α,β-diaminoesters

Viso Beronda, AlmaFernández de la Pradilla, RobertoFlores Aguilar-Amat, AídaLópez Rodríguez, María LuzGarcía Suárez, Ana BeatrizAlonso Rodríguez, Marta Isabel2024-02-022024-02-022004-01-270022-326310.1021/jo035613jhttps://hdl.handle.net/20.500.14352/98460A survey of routes for aminal cleavage of N-sulfinylimidazolidines has been carried out, and selective conditions to cleave the aminal moiety while preserving the sulfinamide group unaltered have been found. Thus, the treatment of enantiopure N-sulfinylimidazolidines with aqueous H3PO4 in THF affords enantiopure N-sulfinyldiamino esters in excellent yields, while the presence of MeOH as cosolvent allows for the simultaneous removal of the sulfinamide group and aminal cleavage. The behavior of these substrates in a variety of chemical transformations has been explored.engFine tuned aminal cleavage: A concise route to differentially protected enantiopure syn-α,β-diaminoestersjournal article1520-6904https://doi.org/10.1021/jo035613jrestricted accessCiencias BiomédicasQuímica orgánica (Farmacia)Química orgánica (Química)23 Química