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Chemoenzymatic Synthesis of the Most Pleasant Stereoisomer of Jessemal
- Source :
- The Journal of Organic Chemistry, 87(9), 6499-6503. AMER CHEMICAL SOC INC
- Publication Year :
- 2022
-
Abstract
- We describe the asymmetric synthesis of the most pleasant enantiomer of Jessemal fragrance. The key steps are (i) the one-pot reduction of an α-chloro-tetrasubstituted cyclohexenone to give the chlorohydrin, catalyzed by two stereoselective redox enzymes (an ene-reductase and an alcohol dehydrogenase); (ii) the regioselective epoxide ring-opening with organocuprate or organolithium nucleophiles. Density functional theory calculations together with the Curtin-Hammett principle allowed the rationalization of the regioselectivity.
- Subjects :
- Organic Chemistry
Epoxy Compounds
Stereoisomerism
Acetates
Pyrans
Subjects
Details
- Language :
- English
- ISSN :
- 00223263
- Database :
- OpenAIRE
- Journal :
- The Journal of Organic Chemistry, 87(9), 6499-6503. AMER CHEMICAL SOC INC
- Accession number :
- edsair.doi.dedup.....e34e0c9ae391b74ac7cedc22a7fd93de