Photo by bermixstudio from unsplash
A copper-catalyzed diastereoselective [4 + 2] cyclolization of α,β-unsaturated ketoxime acetates and trifluoromethyl ketones affords various 3-trifluoromethylated 3-hydroxy-cylcohexan-1-ones smoothly. This reaction features the selective functionalization of a less acidic C(sp3)-H… Click to show full abstract
A copper-catalyzed diastereoselective [4 + 2] cyclolization of α,β-unsaturated ketoxime acetates and trifluoromethyl ketones affords various 3-trifluoromethylated 3-hydroxy-cylcohexan-1-ones smoothly. This reaction features the selective functionalization of a less acidic C(sp3)-H bond by an internal oxdative C(sp3)-H functionalization strategy. Preliminary investigations revealed that α,β-unsaturated ketoxime acetates were an internal oxidant, and the in situ generated H2O served as the O-source of the carbonyl oxygen in the product.
Journal Title: Organic letters
Year Published: 2019
Link to full text (if available)
Share on Social Media: Sign Up to like & get
recommendations!