Abstract
Optically active polyhydroxy trans-1,2-amino alcohols were efficiently synthesized in good to excellent yields by the Petasis boronic-Mannich reaction of an amine, an organoboronic acid, and a chiral lactol, which was prepared from d-araboascorbic acid or its diastereomer. Further transformations of the resulting Petasis products were investigated in detail to obtain chiral building blocks containing three continuous stereogenic centers.
| Original language | English |
|---|---|
| Article number | ss-2014-c0373-op |
| Pages (from-to) | 2672-2681 |
| Number of pages | 10 |
| Journal | Synthesis (Germany) |
| Volume | 46 |
| Issue number | 19 |
| DOIs | |
| Publication status | Published - Oct 1 2014 |
Keywords
- asymmetric synthesis
- chiral pool
- coupling
- diastereoselectivity
- domino reaction
- lactones
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry
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Mandai, H., Yamada, H., Shimowaki, K., Mitsudo, K., & Suga, S. (2014). An Efficient Petasis Boronic-Mannich Reaction of Chiral Lactol Derivatives Prepared from d -Araboascorbic Acid. Synthesis (Germany), 46(19), 2672-2681. [ss-2014-c0373-op]. https://doi.org/10.1055/s-0034-1378900