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

Autor: Motoo Shiro, Tohru Oishi, Masamitsu Ochi, Misako Fukuhara, Tetsushi Gohda, Hiroko Kuzume, Masahiro Hirama, Hiyoshizo Kotsuki
Rok vydání: 1995
Předmět:
Zdroj: Tetrahedron: Asymmetry. 6:2227-2236
ISSN: 0957-4166
DOI: 10.1016/0957-4166(95)00297-3
Popis: 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 C 2 -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 N 2 inversion, and pyrrolidine ring formation via intramolecular substitution as the key steps.
Databáze: OpenAIRE