4.8 Article

Organocatalytic Asymmetric Dearomatization Reaction for the Synthesis of Axial Chiral Allene-Derived Naphthalenones Bearing Quaternary Stereocenters

Journal

ORGANIC LETTERS
Volume 23, Issue 17, Pages 6606-6611

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01849

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Funding

  1. National Natural Science Foundation of China [22071213]
  2. Leading Talents of Special Support Program of Zhejiang Province High-level Talents [2020R52008]
  3. Center of Chemistry for Frontier Technologies of Zhejiang University

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The highly regio-, diastereo-, and enantioselective dearomatization reaction of 1-substituted 2-naphthols and beta,gamma-alkynyl-alpha-imino esters with complete atom economy is disclosed via chiral phosphoric acid catalysis. This protocol provides facile and efficient access to asymmetric construction of axially chiral allene-derived naphthalenones bearing quaternary stereocenters in good yields with high diastereoselectivities and enantioselectivities.
The highly regio-, diastereo-, and enantioselective dearomatization reaction of 1-substituted 2-naphthols and beta,gamma-alkynyl-alpha-imino esters with complete atom economy is disclosed via chiral phosphoric acid catalysis. This protocol provides facile and efficient access to asymmetric construction of a broad range of axially chiral allene-derived naphthalenones bearing quaternary stereocenters in good yields with high diastereoselectivities and enantioselectivities.

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