Chemoselectivity control in the reactions of 1,2-cyclic sulfamidates with amines

  1. Mata, L. 1
  2. Avenoza, A. 1
  3. Busto, J.H. 1
  4. Peregrina, J.M. 1
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    GRID grid.119021.a

Journal:
Chemistry - A European Journal

ISSN: 0947-6539

Year of publication: 2013

Volume: 19

Issue: 21

Pages: 6831-6839

Type: Article

Export: RIS
DOI: 10.1002/chem.201204392 SCOPUS: 2-s2.0-84877768260 WoS: 000318923800035 GOOGLE SCHOLAR lock_openOpen access editor

Metrics

Cited by

  • Scopus Cited by: 12 (12-06-2021)

Journal Citation Reports

  • Year 2013
  • Journal Impact Factor: 5.696
  • Best Quartile: Q1
  • Area: CHEMISTRY, MULTIDISCIPLINARY Quartile: Q1 Rank in area: 22/148 (Ranking edition: SCIE)

SCImago Journal Rank

  • Year 2013
  • SJR Journal Impact: 2.643
  • Best Quartile: Q1
  • Area: Catalysis Quartile: - Rank in area: 10/48
  • Area: Organic Chemistry Quartile: - Rank in area: 8/187
  • Area: Chemistry (miscellaneous) Quartile: Q1 Rank in area: 23/460

CiteScore

  • Year 2013
  • CiteScore of the Journal : 9.6
  • Area: Chemistry (all) Percentile: 95
  • Area: Medicine (all) Percentile: 92

Abstract

Although 1,2-cyclic sulfamidates derived from α-methylisoserine undergo nucleophilic displacement at the quaternary center, to the best of our knowledge their behavior with amines as nucleophiles has never been explored. We have found that a broad range of amines can be used, demonstrating the scope of the reaction, and that excellent control of the chemoselectivity can be achieved. Application of this methodology for the synthesis of a chiral α,β-diamino acid and an important piperazinone heterocycle is also presented. Additionally, we have found that DMF and DMSO behave not only as polar aprotic solvents but also as O-nucleophilic reagents, allowing the incorporation of an oxygen atom at a quaternary center of the electrophile, with inversion of configuration. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.