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
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

  2. 2 University of California Los Angeles
    info

    University of California Los Angeles

    Los Ángeles, Estados Unidos

    ROR https://ror.org/046rm7j60

Journal:
Journal of Organic Chemistry

ISSN: 0022-3263

Year of publication: 2011

Volume: 76

Issue: 10

Pages: 4034-4042

Type: Article

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DOI: 10.1021/JO200479Y SCOPUS: 2-s2.0-79956109949 WoS: WOS:000290465700045 GOOGLE SCHOLAR

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Abstract

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.