Lewis Acid Catalyzed Nucleophilic Ring Opening and 1,3-Bisfunctionalization of Donor–Acceptor Cyclopropanes with Hydroperoxides: Access to Highly Functionalized Peroxy/(α-Heteroatom Substituted)Peroxy Compounds

The Lewis acid catalyzed ring opening
reaction of Donor–Acceptor
(D–A) cyclopropanes with alkyl hydroperoxides is reported to
furnish various peroxycarbonyls and 1,3-haloperoxygenated compounds
in good to excellent yields. This method adds another instance to
scarcely reported noncyclilizing 1,3-bisfunctionalization of D–A
cyclopropanes with two different functional groups and relies on the
dual role of peroxide as nucleophile and oxidant through an orchestrated
reaction sequence. The products obtained, including α-heterosubstituted
peroxy compounds, are amenable to useful synthetic elaboration.