4.8 Article

Base-Accelerated Enantioselective Substitution of Morita-Baylis-Hillman Carbonates with Dialkyl Phosphine Oxides

Journal

ORGANIC LETTERS
Volume 12, Issue 17, Pages 3914-3917

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol101601d

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Funding

  1. NSFC [20932003, 90813012]
  2. National S&T Major Project of China [2009ZX09503-017]

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A base could accelerate the S(N)2' or S(N)2' S(N)2' reaction of Morita-Baylis-Hillman (MBH) carbonates with dialkyl phosphine oxides, but the judicial choice of an appropriate base would greatly depress this competitive S(N)2' reaction and allow for a highly enantioselective allylic substitution reaction with satisfactory yields and excellent enantioselectivities.

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