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Asymmetric synthesis of ?-chloro-?,?-diamino- and ?,?-aziridino-?-aminoacylpyrrolidines and -piperidines via stereoselective Mannich-type additions of N-(diphenylmethylene)glycinamides across ?-chloro-N-sulfinylimines.


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

SUBMITTER: Callebaut G 

PROVIDER: S-EPMC3520569 | biostudies-other | 2012

REPOSITORIES: biostudies-other

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Asymmetric synthesis of γ-chloro-α,β-diamino- and β,γ-aziridino-α-aminoacylpyrrolidines and -piperidines via stereoselective Mannich-type additions of N-(diphenylmethylene)glycinamides across α-chloro-N-sulfinylimines.

Callebaut Gert G   Mangelinckx Sven S   Van der Veken Pieter P   Törnroos Karl W KW   Augustyns Koen K   De Kimpe Norbert N  

Beilstein journal of organic chemistry 20121205


The asymmetric synthesis of new chiral γ-chloro-α,β-diaminocarboxylamide derivatives by highly diastereoselective Mannich-type reactions of N-(diphenylmethylene)glycinamides across chiral α-chloro-N-p-toluenesulfinylaldimines was developed. The resulting (S(S),2S,3S)-γ-chloro-α,β-diaminocarboxylamides were formed with the opposite enantiotopic face selectivity as compared to the (S(S),2R,3R)-γ-chloro-α,β-diaminocarboxyl esters obtained via Mannich-type addition of analogous N-(diphenylmethylene)  ...[more]

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