%0 Journal Article
%T Asymmetric synthesis of ¦Ã-chloro-¦Á,¦Â-diamino- and ¦Â,¦Ã-aziridino-¦Á-aminoacylpyrrolidines and -piperidines via stereoselective Mannich-type additions of N-(diphenylmethylene)glycinamides across ¦Á-chloro-N-sulfinylimines
%A Gert Callebaut
%A Sven Mangelinckx
%A Pieter Van der Veken
%A Karl W. T£¿rnroos
%J Beilstein Journal of Organic Chemistry
%D 2012
%I 
%R 10.3762/bjoc.8.239
%X The asymmetric synthesis of new chiral ¦Ã-chloro-¦Á,¦Â-diaminocarboxylamide derivatives by highly diastereoselective Mannich-type reactions of N-(diphenylmethylene)glycinamides across chiral ¦Á-chloro-N-p-toluenesulfinylaldimines was developed. The resulting (SS,2S,3S)-¦Ã-chloro-¦Á,¦Â-diaminocarboxylamides were formed with the opposite enantiotopic face selectivity as compared to the (SS,2R,3R)-¦Ã-chloro-¦Á,¦Â-diaminocarboxyl esters obtained via Mannich-type addition of analogous N-(diphenylmethylene)glycine esters across a chiral ¦Á-chloro-N-p-toluenesulfinylaldimine. Selective deprotection under different acidic reaction conditions and ring closure of the ¦Ã-chloro-¦Á,¦Â-diaminocarboxylamides was optimized, which resulted in N¦Á-deprotected syn-¦Ã-chloro-¦Á,¦Â-diaminocarboxylamides, N-sulfinyl-¦Â,¦Ã-aziridino-¦Á-aminocarboxylamide derivatives, a trans-imidazolidine, and an N¦Á,N¦Â-deprotected syn-¦Ã-chloro-¦Á,¦Â-diaminocarboxylamide.
%K asymmetric synthesis
%K diaminoacid derivatives
%K Mannich-type addition
%K N-sulfinylimines
%K stereoselectivity
%U http://dx.doi.org/10.3762/bjoc.8.239