Fine-tuned aminal cleavage: a concise route to differentially protected enantiopure syn-alpha,beta-diamino Esters.
A 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 H(3)PO(4) 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.
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Alma
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Instituto de Química Orgánica, Consejo Superior de Investigaciones Científicas, Juan de la Cierva 3, E-28006 Madrid, Spain. iqov379@iqog.csic.es
Fernández de la Pradilla
Roberto
R
López-Rodríguez
María L
ML
García
Ana
A
Flores
Aida
A
Alonso
Marta
M
D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D007093:Imidazoles / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*
D000588:Amines; D004952:Esters; D007093:Imidazoles; D013449:Sulfonamides