1365547-75-6Relevant academic research and scientific papers
Asymmetric synthesis of α,β-diamino acid derivatives with an aziridine-, azetidine- and γ-lactone-skeleton via Mannich-type additions across α-chloro-N-sulfinylimines
Callebaut, Gert,Mangelinckx, Sven,Kiss, Lorand,Sillanpaeae, Reijo,Fueloep, Ferenc,De Kimpe, Norbert
, p. 2326 - 2338 (2012)
The efficient asymmetric synthesis of new chiral γ-chloro-α, β-diamino acid derivatives via highly diastereoselective Mannich-type reactions of N-(diphenylmethylene) glycine esters across a chiral α-chloro-N-p-toluenesulfinylimine was developed. The influence of the base, LDA or LiHMDS, used for the formation of the glycine enolates, was of great importance for the anti-/syn-diastereoselectivity of the Mannich-type reaction. The γ-chloro-α,β-diamino acid derivatives proved to be excellent building blocks for ring closure towards optically pure anti- and syn-β,γ-aziridino-α-amino esters, and subsequent ring transformation into trans-3-aminoazetidine-2-carboxylic acid derivatives and α,β-diamino-γ-butyrolactones. The Royal Society of Chemistry 2012.
Asymmetrie synthesis of y-chloro-α,β-diaminoand β,y-aziridino-α-aminoacylpyrrolidinesand -piperidines via stereoselective Mannich-type additions of N-(diphenylmethylene)glycinamides across α-chloro-N-sulfinylimines
Callebaut, Gert,Mangelinckx, Sven,Van Veken, Pieter Der,Toernroos, Karl W.,Augustyns, Koen,De Kimpe, Norbert
supporting information, p. 2124 - 2131 (2013/02/22)
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
