4.8 Article

LIC-KOR-Promoted Synthesis of Alkoxydienyl Amines: An Entry to 2,3,4,5-Tetrasubstituted Pyrroles

Journal

ORGANIC LETTERS
Volume 11, Issue 17, Pages 3914-3917

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol9015018

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Funding

  1. Italian MIUR
  2. Regione Piemonte

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A stereoselective approach to the synthesis of (E)-alkoxydienylamines (2) is described, starting from alpha,beta-unsaturated acetals (1) and aryl imines, under superbasic conditions. These can be readily converted into alpha-arylglycine derivatives (3) by mild acidic hydrolysis or, in turn, cyclized under oxidative conditions in the presence of a Pd catalyst to 2,3,4,5-tetrasubstituted pyrroles (4).

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