Augustyns, Koen

Callebaut, Gert

De Kimpe, Norbert

Mangelinckx, Sven

Tornroos, Karl W.

van der Veken, Pieter

Abstract: The asymmetric synthesis of new chiral gamma-chloro-alpha,beta-diaminocarboxylamide derivatives by highly diastereoselective Mannich-type reactions of N-(diphenylmethylene) glycinamides across chiral alpha-chloro-N-p-toluenesulfinylaldimines was developed. The resulting (S-S,2S,3S)-gamma-chloro-alpha,beta-diaminocarboxylamides were formed with the opposite enantiotopic face selectivity as compared to the (S-S,2R,3R)-gamma-chloro-alpha,beta-diaminocarboxyl esters obtained via Mannich-type addition of analogous N-(diphenylmethylene) glycine esters across a chiral alpha-chloro-N-p-toluenesulfinylaldimine. Selective deprotection under different acidic reaction conditions and ring closure of the gamma-chloro-alpha,beta-diaminocarboxylamides was optimized, which resulted in N-alpha-deprotected syn-gamma-chloro-alpha,beta-diaminocarboxylamides, N-sulfinyl-beta,gamma-aziridino-alpha-aminocarboxylamide derivatives, a trans-imidazolidine, and an N-alpha,N-beta-deprotected syn-gamma-chloro-alpha,beta-diaminocarboxylamide

Institutional Repository Universiteit Antwerpen

Asymmetric synthesis of \u3b3-chloro-\u3b1, \u3b2-diamino- and \u3b2, \u3b3-aziridino-\u3b1-aminoacylpyrrolidines and -piperidines via stereoselective Mannich-type additions of N-(diphenylmethylene)glycinamides across \u3b1-chloro-N-sulfinylimines

Asymmetric synthesis of \u3b3-chloro-\u3b1, \u3b2-diamino- and \u3b2, \u3b3-aziridino-\u3b1-aminoacylpyrrolidines and -piperidines via stereoselective Mannich-type additions of N-(diphenylmethylene)glycinamides across \u3b1-chloro-N-sulfinylimines

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Institutional Repository Universiteit Antwerpen