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Effective Chiral Ferrocenyl Phosphine-Thioether Ligands in Enantioselective Palladium-Catalyzed Allylic Alkylations

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 351, Issue 9, Pages 1412-1422

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200900086

Keywords

allylic alkylation; asymmetric catalysis; enantioselectivity; ferrocenes; phosphine-thioether ligands

Funding

  1. University Grants Committee Areas of Excellence Scheme [AoE/P-10/01]
  2. Hong Kong Research Grants Council [PolyU5001/08P]
  3. Hong Kong Polytechnic University A SD

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Chiral ferrocene-derived phosphine-thioether mixed donor ligands supported by heterocycles effected the palladium-catalyzed enantioselective allylic alkylations with excellent yields and enantioselectivities (up to 96% ee). With cyclic and unsymmetrical allylic acetates as substrate, the corresponding alkylated products with enantioselectivities up to 87% ee were obtained. Based on X-ray crystallographic and NMR studies, the origin of the observed enantioselectivities is discussed.

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