Stereocontrolled Ring-Opening of a Hindered Sulfamidate with Nitrogen-Containing Aromatic Heterocycles: Synthesis of Chiral Quaternary Imidazole Derivates

  1. Mata, L. 1
  2. Jiménez-Osés, G. 2
  3. Avenoza, A. 1
  4. Busto, J.H. 1
  5. Peregrina, J.M. 1
  1. 1 Universidad de La Rioja

    Universidad de La Rioja

    Logroño, España

    GRID grid.119021.a

  2. 2 University of California Los Angeles

    University of California Los Angeles

    Los Ángeles, Estados Unidos

    GRID grid.19006.3e

Journal of Organic Chemistry

ISSN: 0022-3263

Year of publication: 2011

Volume: 76

Issue: 10

Pages: 4034-4042

Type: Article

Export: RIS
DOI: 10.1021/jo200479y SCOPUS: 2-s2.0-79956109949 WoS: 000290465700045 GOOGLE SCHOLAR


Cited by

  • Scopus Cited by: 20 (12-06-2021)

Journal Citation Reports

  • Year 2011
  • Journal Impact Factor: 4.45
  • Best Quartile: Q1
  • Area: CHEMISTRY, ORGANIC Quartile: Q1 Rank in area: 9/56 (Ranking edition: SCIE)

SCImago Journal Rank

  • Year 2011
  • SJR Journal Impact: 2.265
  • Best Quartile: Q1
  • Area: Organic Chemistry Quartile: Q1 Rank in area: 13/182


  • Year 2011
  • CiteScore of the Journal : 7.7
  • Area: Organic Chemistry Percentile: 92
  • Area: Medicine (all) Percentile: 89


This paper explores the role of a hindered cyclic sulfamidate derived from α-methylisoserine as an electrophile in a nucleophilic displacement reaction with nitrogen-containing aromatic heterocycles. Several imidazoles and pyrazole were tested as nucleophiles in the absence of an additional base to give the corresponding ring-opening compounds. We show that the process takes place by inversion of the configuration of the quaternary electrophilic center, retaining the enantiomeric excess of the starting sulfamidate. This reaction opens the way to obtain important quaternary imidazole derivatives such as an innovative type of bis-amino acid related to histidinoalanine and a novel α,α-disubstituted β-amino acid (β2,2-amino acid). © 2011 American Chemical Society.