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