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Synlett 2001; 2001(1): 0045-0048
DOI: 10.1055/s-2001-9731
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Diastereocontrolled Synthesis of Enantiopure trans- and cis-5-Allylprolinols via a Ring-Contraction Protocol

Hideki Sakagami* , Kunio Ogasawara
  • *Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan; Fax +81-22-217-6845; E-mail: konol@mail.cc.tohoku.ac.jp
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Publication Date:
31 December 2001 (online)

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A highly diastereocontrolled formation of trans- and cis-5-allyl-N-benzylprolinols from trans- and cis-2-allyl-N-benzyl-5-piperidinols has been achieved by employing a ring-contraction protocol.

chiral building block - ring contraction - 2-allyl-5-piperidinol - 5-allylprolinol - cesium acetate - Mitsunobu reaction