4.8 Article

Phosphine-catalyzed enantioselective [3+2] cycloadditions of γ-substituted allenoates with β-perfluoroalkyl enones

Journal

CHEMICAL SCIENCE
Volume 8, Issue 6, Pages 4660-4665

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c7sc01432e

Keywords

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Funding

  1. 973 Programs [2015CB856600]
  2. National Natural Science Foundation of China [21372084, 21425205, 21672067]
  3. Changjiang Scholars and Innovative Research Team in University (PCSIRT)

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The enantioselective construction of densely functionalized cyclopentene bearing contiguous three stereocenters has been a challenging task in organic synthesis. Herein, we present a phoshine-catalyzed highly regio-, diastereo- and enantioselective [3 + 2] cycloaddition of gamma-substituted allenoates with beta-perfluoroalkyl enones, delivering a wide range of densely functionalized perfluoroalkylated cyclopentenes with three contiguous chiral stereocenters.

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