4.8 Article

C-H Oxidation/Michael Addition/Cyclization Cascade for Enantioselective Synthesis of Functionalized 2-Amino-4H-chromenes

Journal

ORGANIC LETTERS
Volume 17, Issue 24, Pages 6134-6137

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b03148

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Funding

  1. National Natural Science Foundation of China [21372220, 21532006]

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A streamlined method for the enantioselective synthesis of 2-amino-4H-chromenes from readily available 2-alkyl-substituted phenols and active methylene compounds bearing a cyano group with up to 97% ee is presented. This reaction is a cascade procedure including manganese dioxide mediated CH oxidation for the generation of o-quinone methides and bifunctional squaramide-catalyzed Michael addition/cyclization.

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