4.8 Article

Catalytic Enantioselective Oxidative Cross-Coupling of Benzylic Ethers with Aldehydes

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 2, Pages 543-547

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201308701

Keywords

aldehydes; asymmetric catalysis; benzylic ethers; CH functionalization; organocatalysis

Funding

  1. National Science Foundation of China [21202093, 30925038]
  2. Young Scientist Foundation Grant of Shandong Province [BS2013YY001]

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The first one-pot enantioselective oxidative coupling of cyclic benzylic ethers with aldehydes has been developed. A variety of benzylic ethers were transformed into the corresponding oxygen heterocycles with high enantioselectivity. Mechanistic experiments were conducted to determine the nature of the reaction intermediates. The application of this strategy to coupling reactions with other nucleophiles besides aldehydes was also explored.

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