4.8 Article

Diastereoselective Room-Temperature Pd-Catalyzed α-Arylation and Vinylation of Arylmandelic Acid Derivatives

Journal

ORGANIC LETTERS
Volume 11, Issue 7, Pages 1543-1546

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol900131q

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Funding

  1. NCI [T32CA09112]
  2. DFG awards [WE 3549/2-1]
  3. National Institutes of Health [GM 1S10RR13886-01]

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Palladium-catalyzed alpha-arylation and vinylation of dioxolane (S,S)-I, easily obtained from (S)-mandelic acid, proceeds with high yields and excellent diastereoselectivity at room temperature employing commercially available P(t-Bu)(3)center dot HBF4 and Pd(OAc)(2) as a catalytic precursor system. This method displays general utility for a large variety of aryl, heteroaryl, and vinyl bromides.

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