Synthesis of novel polysubstituted N-benzyl-1H-pyrroles via a cascade reaction of alkynyl Fischer carbenes with α-imino glycine methyl esters

Org Biomol Chem. 2015 Dec 28;13(48):11753-60. doi: 10.1039/c5ob01655j. Epub 2015 Oct 21.

Abstract

An efficient and simple synthesis of novel and densely substituted N-benzyl-1H-pyrroles 6a-r is described by a 1,4-addition/isomerization/ring closure/demetalation cascade process of alkynyl Fischer carbene complexes 1a-f and 2a and α-imino glycine methyl esters 3a, b, d, g, h, and k promoted with LDA.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Glycine / analogs & derivatives*
  • Glycine / chemistry
  • Imines / chemistry*
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Molecular Structure
  • Pyrroles / chemical synthesis*

Substances

  • Imines
  • Pyrroles
  • carbene
  • glycine methyl ester
  • Methane
  • Glycine