4.8 Article

Palladium-Catalyzed Asymmetric Tandem [3+2] Cycloaddition/Allylation Reaction of Methylene-Trimethylenemethane: Access to Chiral Tricyclic Dinitrogen-Fused Heterocycles

Journal

ORGANIC LETTERS
Volume 21, Issue 12, Pages 4424-4427

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b01064

Keywords

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Funding

  1. Natural Science Foundation of China [21572264, 21871293]
  2. Chinese Universities Scientific Fund [2018TC052, 2018TC055, 2019TC085]

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A palladium-catalyzed asymmetric tandem [3+2] cycloaddition/allylation of methylene-trimethylenemethane is presented, providing the functionalized chiral hexahydropyrazolo[5,1-a]isoquinoline derivatives in high yields with good to excellent enantioselectivities and moderate to good E:Z ratios. In the one-pot sequential tandem reactions/hydroxylation, (E)-allylic alcohol products were obtained in good yields with excellent enantioselectivities.

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