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

    ROR https://ror.org/0553yr311

Revue:
Chemistry - A European Journal

ISSN: 0947-6539

Année de publication: 2013

Volumen: 19

Número: 21

Pages: 6831-6839

Type: Article

DOI: 10.1002/CHEM.201204392 SCOPUS: 2-s2.0-84877768260 WoS: WOS:000318923800035 GOOGLE SCHOLAR lock_openAccès ouvert editor

D'autres publications dans: Chemistry - A European Journal

Projets liés

Diseño racional de glicopéptidos con aplicaciones en Química Biológica

2013/00007/001

Síntesis y análisis conformacional de O-Glicopéptidos de interés estructural y biológico.

2009/00205/001

Résumé

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.