4.5 Article

Chiral Bis(NHC)-Palladium(II) Complex Catalyzed and Diethylzinc-Mediated Enantioselective Umpolung Allylation of Aldehydes

Journal

ORGANOMETALLICS
Volume 28, Issue 8, Pages 2640-2642

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/om900109m

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Funding

  1. Shanghai Municipal Committee of Science and Technology [06XD14005, 08dj 1400100-2]
  2. National Basic Research Program of China [(973)-2009CB825300]
  3. National Natural Science Foundation of China [20872162, 20672127, 20821002, 20732008]

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A series of chiral bis(NHC)-Pd(II) complexes bearing different coordinating counterions have been prepared and successfully applied in Et2Zn-mediated enantioselective umpolung allylation of aldehydes with cyclohexenyl acetate, affording the homoallylic alcohols in moderate to excellent yields (lip to 96%), modest enantioselectivities (54%-66% ee), and good to excellent syn diastereoselectivities (up to 99:1 dr).

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