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Asymmetric synthesis of (2S,3S)- and (2S,3R)-3-prolinomethionines: 3-methylsulfanylmethyl-pyrrolidine-2-carboxylic acids

✍ Scribed by Philippe Karoyan; Gérard Chassaing

Publisher: Elsevier Science
Year: 1997
Tongue: English
Weight: 547 KB
Volume: 8
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(97)00203-6

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✦ Synopsis

The synthesis of 3-prolinomethionine can be easily achieved in a diastereoselective and enantioselective way via zinc-enolate cyclisation. After transmetallation by CuCN.2LiCI, the zinc--copper derivative was reacted with S-methyl methanesulfonothioate leading in a "one-pot" procedure, to N-(0t-methylbenzyl)-3-prolinomethionine benzyl ester. The ot-methylbenzyl group was transformed in vinyl-oxycarbonyl and tertiobutyloxycarbonyl groups successively. Reprotonation of cis Voc prolinomethionine enolate at low temperature yielded the enantiomerically pure trans diastereoisomer, t~) 1997 Elsevier Science Ltd

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