4.8 Article

Convergent Synthesis of Enantioenriched ortho-Fused Tricyclic Diketones via Catalytic Asymmetric Intramolecular Vinylogous Aldol Condensation

Journal

ORGANIC LETTERS
Volume 24, Issue 49, Pages 9017-9022

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c03645

Keywords

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Funding

  1. National Natural Science Foundation of China
  2. Chinese Universities Scientific Fund
  3. Scientific Fund of North-west AF University
  4. [22171229]
  5. [21722206]
  6. [21572182]

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In this study, a catalytic asymmetric intramolecular vinylogous aldol reaction using dual organocatalysts was described, allowing for the convergent synthesis of ortho-fused tricyclic diketones with excellent enantioselectivities and diastereoselectivities. Notably, the reaction selectively generates three consecutive stereogenic carbon centers, including a quaternary one. Density functional theory calculations revealed that the enhanced enantioselectivity was facilitated by a transannular hydrogen bonding between the protonated quinuclidine moiety of the chiral aminocatalyst and the diketone fragment of the substrate.
Herein, we describe a catalytic asymmetric intramolecular vinylogous aldol reaction by taking advantage of dual organocatalysts, which enables convergent synthesis of ortho-fused tricyclic diketones in excellent enantioselectivities and diastereoselectivities. Noteworthy is that the reaction stereoselectively forges three consecutive stereogenic carbon centers including a quaternary one. Density functional theory calculations reveal that the enantioselectivity was facilitated by a transannular hydrogen bonding between the protonated quinuclidine moiety of the chiral aminocatalyst and the diketone fragment of the substrate.

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