4.4 Article

Enantioselective synthesis of nitrocyclopropanes via conjugate addition of bromomalonate to nitroalkenes catalyzed by Ni(II) complexes

Journal

TETRAHEDRON LETTERS
Volume 53, Issue 27, Pages 3437-3439

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2012.04.072

Keywords

Cyclopropanation; Asymmetric catalysis; Chiral nickel catalysts; Nitroalkenes; Conjugate addition

Funding

  1. National Research Foundation of Korea (NRF)
  2. Ministry of Education, Science and Technology [2011-0002488]

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A novel one-pot methodology for the catalytic enantioselective synthesis of highly functionalized nitrocyclopropanes promoted by chiral nickel complexes is developed. The treatment of bromomalonates with nitroalkenes under the mild reaction conditions afforded the corresponding Michael adducts which cyclizes to controlled reaction conditions with excellent diasteroselectivities (>99 de) and enantioselectivities (up to 99% ee). (C) 2012 Elsevier Ltd. All rights reserved.

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