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

Research output: Contribution to journal › Article › peer-review

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
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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

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.",

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

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T1 - New convenient, enantiospecific synthesis of (S,S)- and (R,R)-2,2′-bipyrrolidine derivatives

AU - Kotsuki, Hiyoshizo

AU - Kuzume, Hiroko

AU - Gohda, Tetsushi

AU - Fukuhara, Misako

AU - Ochi, Masamitsu

AU - Oishi, Tohru

AU - Hirama, Masahiro

AU - Shiro, Motoo

PY - 1995/9

Y1 - 1995/9

N2 - 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.

AB - 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.

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ER -

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

Abstract

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