4.7 Article

Asymmetric organocatalytic multicomponent reactions for efficient construction of bicyclic compounds bearing bisacetal and isoxazolidine moieties

Journal

CHEMICAL COMMUNICATIONS
Volume 56, Issue 84, Pages 12765-12768

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d0cc05099g

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Funding

  1. National Science and Technology Major Project for Significant New Drugs Development [2018ZX09735004]
  2. Scientific and Technological Innovation Project - Qingdao National Laboratory for Marine Science and Technology [2015ASKJ02-06]
  3. NSFC-Shandong Joint Fund for Marine Science Research Centers [U1606403]

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An organocatalytic multicomponent reaction ofN-protected hydroxylamines, acrylaldehyde and acetal-containing enones was developed. Bisacetal-containing bicyclic isoxazolidine derivatives bearing four continuous stereocenters were formed with excellent stereoselectivities. A plausible reaction pathway was proposed based on(18)O-labeling control experiments.

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