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Updated: May 13, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Intramolecular C-H Functionalization of α-Alkyl-α-diazoesters toward the Synthesis of Lactones
Bijaya Bagale1, Aubree L Nolan1, Elizabeth U Heuser1
1Department of Chemistry and Biochemistry, Kent State University, Kent, Ohio 44242, United States.
Abstract:
Intramolecular C-H functionalization was achieved using rhodium catalysis with α-alkyl-α-diazoesters. Dirhodium tetratriphenylacetate (Rh2(TPA)4), a sterically bulky achiral catalyst, was found to enable the formation of lactones. Alkyl γ-lactones were synthesized in excellent yields and diastereoselectivity, and a diverse array of disubstituted lactones (γ, δ, and ε) were synthesized with good yields and diastereoselectivity. This chemistry was extended to intramolecular C-H insertion in late-stage functionalization with excellent regio- and diastereoselectivity.
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