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 |
|---|---|
| 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
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Cite this
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, 6(9), 2227-2236. https://doi.org/10.1016/0957-4166(95)00297-3