4.8 Article

Asymmetric Reductive and Alkynylative Heck Bicyclization of Enynes to Access Conformationally Restricted Aza[3.1.0]bicycles

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 27, Pages 10814-10818

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202000859

Keywords

alkynylation; azabicycles; palladium; reductive Heck reaction; strained rings

Funding

  1. Peking University Shenzhen Graduate School, Shenzhen Bay Laboratory [21230011-Scripps]
  2. National Natural Science Foundation of China [NSFC 21933004]
  3. Nanyang Technological University
  4. GSK-EDB Trust Fund (2017 GSK-EDB Green and Sustainable Manufacturing Award)
  5. A*STAR Science and Engineering Research Council [AME IRG A1783c0010]

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Conformationally restricted azabicycles are becoming increasingly important in medicinal research. Asymmetric Heck bicyclization of enynes proceeds to give medicinally useful aza[3.1.0] and aza[4.1.0] bicycles with excellent enantioselectivity. The key organopalladium species after bicyclization can be trapped by silanes and terminal alkynes.

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