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 language | English |
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Pages (from-to) | 2227-2236 |
Number of pages | 10 |
Journal | Tetrahedron: Asymmetry |
Volume | 6 |
Issue number | 9 |
DOIs | |
Publication status | Published - Sep 1995 |
Externally published | Yes |
All Science Journal Classification (ASJC) codes
- Catalysis
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry