New convenient, enantiospecific synthesis of (S,S)- and (R,R)-2,2′-bipyrrolidine derivatives

Hiyoshizo Kotsuki, Hiroko Kuzume, Tetsushi Gohda, Misako Fukuhara, Masamitsu Ochi, Tohru Oishi, Masahiro Hirama, Motoo Shiro

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

An enantiomeric pair of (S,S)- and (R,R)-bipyrrolidine derivatives has been prepared from D- and L-tartaric acids or D-mannitol as optically active starting materials. Taking advantage of the C2-symmetric nature of these chiral sources, the synthetic sequence has been established by using efficient side chain elongation, stereospecific conversion of a vicinal diol into a diazido group via SN2 inversion, and pyrrolidine ring formation via intramolecular substitution as the key steps.

Original languageEnglish
Pages (from-to)2227-2236
Number of pages10
JournalTetrahedron: Asymmetry
Volume6
Issue number9
DOIs
Publication statusPublished - Sep 1995
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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