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

Mukherjee, Subrata ; Ghosh, Arghya ; Marelli, Udaya Kiran ; Biju, Akkattu T. (2018) N-Heterocyclic Carbene-Catalyzed Michael–Michael–Lactonization Cascade for the Enantioselective Synthesis of Tricyclic δ-Lactones Organic Letters, 20 (10). pp. 2952-2955. ISSN 1523-7060

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Official URL: http://doi.org/10.1021/acs.orglett.8b00998

Related URL: http://dx.doi.org/10.1021/acs.orglett.8b00998

Abstract

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.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society
ID Code:128628
Deposited On:03 Nov 2022 06:48
Last Modified:03 Nov 2022 06:48

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