4.8 Article

Construction of Quaternary Stereogenic Carbon Centers through Copper-Catalyzed Enantioselective Allylic Alkylation of Azoles

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 15, Pages 4777-4780

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201600619

Keywords

allylic compounds; asymmetric catalysis; carbenes; copper; heterocycles

Funding

  1. JSPS [15H03803]
  2. CREST, JST
  3. ACT-C, JST
  4. Grants-in-Aid for Scientific Research [15H03803] Funding Source: KAKEN

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Copper-catalyzed enantioselective allylic alkylation of azoles with ,-disubstituted primary allylic phosphates was achieved using a new chiral N-heterocyclic carbene ligand bearing a naphtholic hydroxy group. This reaction occurred with excellent branch regioselectivity and high enantioselectivity, thus forming a controlled all-carbon quaternary stereogenic center at the position to the heteroaromatic ring.

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