4.7 Article

Investigation of the Configurational Stabilities of Chiral Isocyanoacetates in Multicomponent Reactions

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 24, Pages 10279-10285

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo201817k

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Funding

  1. Brown University
  2. Royce

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Isocyanoacetates are uniquely reactive compounds characterized by an ambivalent isocyano functional group and an enolizable alpha-carbon. It is widely believed that chiral alpha-substituted isocyanoacetates are configurationally unstable in some synthetically useful isocyanide-based multicomponent reactions. Herein, we demonstrate that chiral isocyanoacetates can be used with minimal to negligible epimerization in a variety of canonical Ugi four-component condensations as well as Joullie-Ugi three-component condensations, reactions that are particularly useful for constructing complex peptide structures in a single synthetic operation.

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