Tetrahedron Asymmetry p. 2025 - 2032 (1997)
Update date:2022-08-03
Topics:
Karoyan, Philippe
Chassaing, Gerard
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.
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