4.8 Article

Asymmetric Homoenolate Additions to Acyl Phosphonates through Rational Design of a Tailored N-Heterocyclic Carbene Catalyst

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 1, Pages 76-79

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja410932t

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Funding

  1. NIH [RO1-GM073072]
  2. Oregon State University

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A highly selective NHC-catalyzed synthesis of gamma-butyrolactones from the fusion of enals and alpha-ketophosphonates has been developed. Computational modeling of competing transition states guided a rational design strategy to achieve enhanced levels of enantioselectivity with a new tailored C-1-symmetric biaryl-saturated imidazolium-derived NHC catalyst.

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