A Short and Elegant Synthesis of (+/-)-Streptopyrrolidine

作者:Shaameri Zurina; Ali Sharifah Hidayah Sharif; Mohamat Mohd Fazli; Yamin Bohari M; Hamzah Ahmad Sazali*
来源:Journal of Heterocyclic Chemistry, 2013, 50(2): 320-325.
DOI:10.1002/jhet.1078

摘要

A brief and efficient approach for the synthesis of (+/-)-5-benzyl-4-hydroxy-2-pyrrolidine () from phenylalanine racemate is described. The key step is the stereocontrolled reduction of the keto functionality of benzylated pyrrolidinone intermediate () via sodium borohydride in carboxylic acid medium furnishing both (R,R)- and (S,S)-configured diastereomers. The natural (R,R) enantiomer (), however, crystallized out from its racemic mixture. Structure of was confirmed by NMR, IR, elemental analyzer, and single crystal X-ray crystallographic techniques.

  • 出版日期2013-3

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