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

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mannitol
Mannitol
elongation
Elongation
Substitution reactions
substitutes
inversions
Derivatives
acids
Acids
rings
synthesis
tartaric acid
pyrrolidine

All Science Journal Classification (ASJC) codes

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

Cite this

New convenient, enantiospecific synthesis of (S,S)- and (R,R)-2,2′-bipyrrolidine derivatives. / Kotsuki, Hiyoshizo; Kuzume, Hiroko; Gohda, Tetsushi; Fukuhara, Misako; Ochi, Masamitsu; Oishi, Tohru; Hirama, Masahiro; Shiro, Motoo.

In: Tetrahedron: Asymmetry, Vol. 6, No. 9, 09.1995, p. 2227-2236.

Research output: Contribution to journalArticle

Kotsuki, H, Kuzume, H, Gohda, T, Fukuhara, M, Ochi, M, Oishi, T, Hirama, M & Shiro, M 1995, 'New convenient, enantiospecific synthesis of (S,S)- and (R,R)-2,2′-bipyrrolidine derivatives', Tetrahedron: Asymmetry, vol. 6, no. 9, pp. 2227-2236. https://doi.org/10.1016/0957-4166(95)00297-3
Kotsuki, Hiyoshizo ; Kuzume, Hiroko ; Gohda, Tetsushi ; Fukuhara, Misako ; Ochi, Masamitsu ; Oishi, Tohru ; Hirama, Masahiro ; Shiro, Motoo. / New convenient, enantiospecific synthesis of (S,S)- and (R,R)-2,2′-bipyrrolidine derivatives. In: Tetrahedron: Asymmetry. 1995 ; Vol. 6, No. 9. pp. 2227-2236.
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