Abstract
Recent advancements in bio-inspired Mn-catalyzed directed oxidations of carboxylic acids have provided promising pathways for the synthesis of a wide variety of chiral Ɣ-lactones. In our current study, however, we have established a catalytic route using 0.25 mol% of electron-rich Mn-complex (MndMMbpbp) that redirects the lactonization reaction to the δ-position, with high enantiomeric excess (over 80%). To the best of our knowledge, enantioselective oxidative δ-lactonizations have not been reported earlier using a transition metal-catalyzed pathway. Our methodology can be extended to the enantioselective synthesis of benzo-fused δ-lactones (up to 70% yield and 62% ee).
Supplementary materials
Title
Strategic functionalization of benzylic C(sp3)–H bonds: Unlocking the potential for Enantioselective δ-lactonization
Description
Materials and methods describing the preparation of complexes and substrates, characterization, reaction optimization and experimental procedures for the catalytic reactions. NMR spectra, MS, IR, SCF and GC traces.
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