Abstract
Preparation of both enantiomeric methyl jasmonates 1 was achieved via lipase-catalyzed resolution of (±)-methyl 7-epicucurbate 3. Lipase P (Amano) provided good selectivity both for acylation of (±)-3 (E = 370) and hydrolysis of the corresponding acetate (E = 41). Resolution of (±)-methyl 6,7-diepicucurbate 2 gave poor results. It was found that the (6R,7S)-configuration was suitable for the selective enzymatic reaction and the C-(3) stereochemistry of the substrate did not influence the enzymatic reaction.
| Original language | English |
|---|---|
| Pages (from-to) | 1035-1038 |
| Number of pages | 4 |
| Journal | Tetrahedron Asymmetry |
| Volume | 12 |
| Issue number | 7 |
| DOIs | |
| Publication status | Published - May 8 2001 |
| Externally published | Yes |
ASJC Scopus subject areas
- Catalysis
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry
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Kiyota, H., Higashi, E., Koike, T., & Oritani, T. (2001). Lipase-catalyzed preparation of both enantiomers of methyl jasmonate. Tetrahedron Asymmetry, 12(7), 1035-1038. https://doi.org/10.1016/S0957-4166(01)00169-0