193538-84-0Relevant academic research and scientific papers
Asymmetric synthesis of (2S,3S)- and (2S,3R)-3-prolinomethionines: 3-Methylsulfanylmethyl-pyrrolidine-2-carboxylic acids
Karoyan, Philippe,Chassaing, Gerard
, p. 2025 - 2032 (2007/10/03)
The synthesis of 3-prolinomethionine can be easily achieved in a diastereoselective and enantioselective way via zinc-enolate cyclisation. After transmetallation by CuCN.2LiCl, the zinc-copper derivative was reached with S-methyl methanesulfonothioate leading in a 'one-pot' procedure, to N-(α-methylbenzyl)-3-prolinomethinine benzyl ester. The α-methylbenzyl group was transformed in vinyl-oxycarbonyl and tertiobutyl-oxycarbonyl groups successively. Reprotonation of cis Voc prolinomethionine enolate at low temperature yielded the enantiomerically pure trans diastereoisomer.
