4.8 Article

Evaluation of Achiral Templates with Fluxional Bronsted Basic Substituents in Enantioselective Conjugate Additions

Journal

ORGANIC LETTERS
Volume 16, Issue 24, Pages 6440-6443

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol503275w

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Funding

  1. NSF [CHM-0709061]
  2. NDSU

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Enantioselective conjugate addition of malononitrile to pyrazolidinone-derived enoates proceeds in excellent yields and high enantioselectivities. A comparison of fluxional substituents with and without a Bronsted basic site and their impact on selectivity is detailed. Molecular sieves as an additive were found to be essential to achieve high enantioselectivity.

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