TY - JOUR
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
N1 - Copyright:
Copyright 2014 Elsevier B.V., All rights reserved.
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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U2 - 10.1016/0957-4166(95)00297-3
DO - 10.1016/0957-4166(95)00297-3
M3 - Article
AN - SCOPUS:0029164921
VL - 6
SP - 2227
EP - 2236
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
SN - 0957-4166
IS - 9
ER -