4.5 Article

Palladium-Catalyzed Allylic Cycloaddition of Vinylethylene Carbonates with 3-Nitrochromone

Journal

ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 10, Issue 3, Pages 545-548

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202000714

Keywords

asymmetric catalysis; Pd-catalyzed asymmetric cycloaddition; furanochromanone; vinylethylene carbonates

Funding

  1. National Natural Science Foundation of China [21871179]
  2. Shanghai Jiao Tong University

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An efficient method for the enantio- and diastereoselective formation of furanochromanones has been developed via Pd-catalyzed asymmetric allylic cycloaddition of vinylethylene carbonates with 3-nitrochromone, yielding products with versatile nitro-group and multi-stereocenters in high yields with excellent enantioselectivities and moderate diastereoselectivities.
An efficient method for the enantio- and diastereoselective formation of furanochromanones has been developed via Pd-catalyzed asymmetric allylic cycloaddition of vinylethylene carbonates with 3-nitrochromone. By using a palladium complex generated in situ from [Pd-2(dba)(3)].CHCl3 and phosphoramidite L4 as a catalyst, the transformation allows to rapid access furanochromanones bearing versatile nitro-group and multi-stereocenters in high yields with excellent enantioselectivities and moderate diastereoselectivities.

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