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Synthesis of Multi-Substituted Pyrroles by Lewis Acid Promoted Cyclization Of N-Sulfonyl Vinylogous Carbamates and Amides

SSRN, ISSN: 1556-5068
2023
  • 1
    Citations
  • 296
    Usage
  • 0
    Captures
  • 0
    Mentions
  • 0
    Social Media
Metric Options:   Counts1 Year3 Year

Metrics Details

  • Citations
    1
    • Citation Indexes
      1
  • Usage
    296
    • Abstract Views
      231
    • Downloads
      65
  • Ratings
    • Download Rank
      696,744

Article Description

A three-step sequence to construct pyrroles from three components including 2,2-dimethoxyethylamine, aryl/alkyl sulfonyl chlorides and alkynes bearing electron-withdrawing groups is presented. The pyrroles are proposed to arise via a 5-exo-trig cyclization proceeding through both oxocarbenium and N-sulfonyliminium ions. This modular route allows for the variability at the N-sulfonyl group, the C2 and C3 substituents for rational vectoring of the pyrrole nucleus for downstream processes.

Bibliographic Details

Matthew Garrett Donahue; Gavin J. Rustin

Elsevier BV

Multidisciplinary; acetal; cyclization; elimination; heterocycles; Lewis acid; N-sulfonyliminium ion; Nitrogen; oxocarbenium ion; pyrrole; sulfonamide; trapping

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