Enantioselective NHC-Catalyzed Redox [4 + 2]-Hetero-Diels-Alder Reactions Using α,β-Unsaturated Trichloromethyl Ketones as Amide Equivalents.

The Journal of Organic Chemistry
Nassilia AttabaAndrew D Smith

Abstract

α,β-Unsaturated trichloromethyl ketones are suitable α,β-unsaturated amide and ester equivalents in N-heterocyclic carbene (NHC)-catalyzed redox hetero-Diels-Alder reactions with azolium enolates generated from α-aroyloxyaldehydes. The initially formed syn-dihydropyranone products can be isolated or can undergo ring-opening with benzylamine followed by aminolysis of the resulting CCl3 ketone to form a range of diamides with high diastereo- and enantioselectivity (up to >95:5 dr and >99% ee).

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Citations

May 29, 2020·Chemical Communications : Chem Comm·Ram Subhawan VermaBhoopendra Tiwari
Jul 25, 2020·Beilstein Journal of Organic Chemistry·Alyn T DaviesAndrew D Smith
Oct 28, 2017·The Journal of Organic Chemistry·Hongbo ZhuJinmao You
Nov 17, 2021·The Journal of Organic Chemistry·Chandra Bhan PandeyBhoopendra Tiwari

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