N‑Heterocyclic Carbene-Catalyzed Michael–Michael–Lactonization Cascade for the Enantioselective Synthesis of Tricyclic δ‑Lactones

Enantioselective synthesis of tricyclic δ-lactones with three contiguous stereocenters has been demonstrated by the N-heterocyclic carbene (NHC)-catalyzed functionalization of benzylic C­(sp3)–H bonds. The NHC-catalyzed reaction of enals with dinitrotoluene derivatives under oxidative conditions pro...

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Bibliographic Details
Published in:Organic letters 2018-05, Vol.20 (10), p.2952-2955
Main Authors: Mukherjee, Subrata, Ghosh, Arghya, Marelli, Udaya Kiran, Biju, Akkattu T
Format: Article
Language:English
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Summary:Enantioselective synthesis of tricyclic δ-lactones with three contiguous stereocenters has been demonstrated by the N-heterocyclic carbene (NHC)-catalyzed functionalization of benzylic C­(sp3)–H bonds. The NHC-catalyzed reaction of enals with dinitrotoluene derivatives under oxidative conditions proceeds via the chiral α,β-unsaturated acylazoliums and produces the δ-lactones in good yields and excellent diastereoselectivity and enantioselectivity. This mild and atom-economic cascade reaction takes place in a Michael/Michael/lactonization sequence and tolerates a broad range of functional groups.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b00998