ArticleThe Journal of organic chemistry2022
Chemoenzymatic Synthesis of the Most Pleasant Stereoisomer of Jessemal.
Article in The Journal of organic chemistry, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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2 citing papers in PubMed.
- Multigram-Scale Asymmetric Alkene Reduction Catalyzed by a Thermostable Flavin Ene-Reductase.Organic process research & development · 2026Article
- Synthesis of Optically ActiveOrganic letters · 2022Article
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8 authors.
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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.
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