1365548-29-3

Upstream product

• 188447-91-8 (S)-p-toluenesulfinimide 
• 1365548-20-4 (S(S),2R,3R)-methyl 2-(diphenylmethyleneamino)-4-chloro-4-methyl-3-(p-toluenesulfinylamino)pentanoate 
• 1365547-75-6 (S_S)-α-chloro-N-p-toluenesulfinyl isobutyraldimine 
• 81167-39-7 methyl N-(diphenylmethylene)glycinate 

Relevant 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

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.