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Communication | Regular issue | Vol 19, No. 8, 1982, pp.1443-1447
Published online, 1st January, 1970
DOI: 10.3987/R-1982-08-1443
Enantiomeric Synthesis of 2-Allyl-4-hydroxypyrrolidine Framework via Iodine-mediated Reaction

Seiichi Takano, Chiyoshi Kasahara, and Kunio Ogasawara

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


The amide (14), prepared from the symmetric amine (12) and a chiral acid, (S)-(—)-proline, furnished a mixture of the epimeric (2S,4R/S)-(—)-2-allyl-4-hydroxypyrrolidine derivatives in good yieid upon reaction with iodine in an aqueous solvent. Chiralities of the both products are established by correlating them to (2S,4R)-(—)-4-hydroxyproline (27).