Highly chemoselective reactions on hindered sulfamidates with oxygenated nucleophiles

  1. Jiménez-Osés, G. 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

Revista:
Tetrahedron: Asymmetry

ISSN: 0957-4166

Año de publicación: 2008

Volumen: 19

Número: 4

Páginas: 443-449

Tipo: Artículo

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DOI: 10.1016/J.TETASY.2008.01.030 SCOPUS: 2-s2.0-39949083736 WoS: WOS:000255350500007 GOOGLE SCHOLAR

Otras publicaciones en: Tetrahedron: Asymmetry

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Resumen

Although the chemoselectivity problems in substitution reactions, which arise from the use of oxygenated nucleophiles in a basic medium by generating anionic species are well-known, we report herein a highly chemoselective ring-opening reaction of hindered cyclic sulfamidates with O-nucleophiles. The reaction occurs with the inversion of configuration at the quaternary centre, allowing the stereoselective synthesis of an important class of β2,2-amino acids, namely O-substituted α-methylisoserines. © 2008 Elsevier Ltd. All rights reserved.