Asymmetric synthesis of ,-diamino acid derivatives with an aziridine-, azetidine- and -lactone-skeleton via Mannich-type additions across -chloro-N-sulfinyliminesElectronic supplementary information (ESI) available. See DOI: 10.1039/c2ob06637h

The efficient asymmetric synthesis of new chiral -chloro-,-diamino acid derivatives via highly diastereoselective Mannich-type reactions of N -(diphenylmethylene) glycine esters across a chiral -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 -chloro-,-diamino acid derivatives proved to be excellent building blocks for ring closure towards optically pure anti - and syn -,-aziridino--amino esters, and subsequent ring transformation into trans -3-aminoazetidine-2-carboxylic acid derivatives and ,-diamino--butyrolactones. New chiral syn - and anti --chloro-,-diamino esters are formed in high yield and in excellent diastereomeric ratios via stereoselective Mannich-type reactions of N -(diphenylmethylene) glycine esters across a chiral -chloro- N-p -toluenesulfinylimine.