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

doi:10.1016/0957-4166(95)00297-3

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

Organic and Biological Chemistry

Research output: Contribution to journal › Article

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 S_N2 inversion, and pyrrolidine ring formation via intramolecular substitution as the key steps.

Original language	English
Pages (from-to)	2227-2236
Number of pages	10
Journal	Tetrahedron: Asymmetry
Volume	6
Issue number	9
DOIs	https://doi.org/10.1016/0957-4166(95)00297-3
Publication status	Published - 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

Kotsuki, H., Kuzume, H., Gohda, T., Fukuhara, M., Ochi, M., Oishi, T., ... Shiro, M. (1995). New convenient, enantiospecific synthesis of (S,S)- and (R,R)-2,2′-bipyrrolidine derivatives. Tetrahedron: Asymmetry, 6(9), 2227-2236. https://doi.org/10.1016/0957-4166(95)00297-3

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 journal › Article

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 H, Kuzume H, Gohda T, Fukuhara M, Ochi M, Oishi T et al. New convenient, enantiospecific synthesis of (S,S)- and (R,R)-2,2′-bipyrrolidine derivatives. Tetrahedron: Asymmetry. 1995 Sep;6(9):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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