4.8 Article

Horner-Wadsworth-Emmons Reagents as Azomethine Ylide Analogues: Pyrrole Synthesis via (3+2) Cycloaddition

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ORGANIC LETTERS
卷 12, 期 21, 页码 4916-4919

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AMER CHEMICAL SOC
DOI: 10.1021/ol102075y

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  1. NSERC
  2. FQRNT
  3. CFI

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Amido-substituted Horner-Wadsworth-Emmons reagents can serve as precursors to 1,3-dipoles for use in cycloaddition. These compounds are assembled in one pot via the TMSOTf-catalyzed Arbuzov reaction of imines, acid chlorides, and phosphites. The coupling of this synthesis with alkyne cycloaddition provides a three-component synthesis of pyrroles. The dipoles can be prepared with a diverse range of imines and acid chlorides, and (3 + 2) cycloaddition with unsymmetrical alkynes is highly regiospecific, providing a modular approach to form substituted pyrroles.

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