Highly chemoselective reactions on hindered sulfamidates with oxygenated nucleophiles
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Universidad de La Rioja
info
ISSN: 0957-4166
Any de publicació: 2008
Volum: 19
Número: 4
Pàgines: 443-449
Tipus: Article
Altres publicacions en: Tetrahedron: Asymmetry
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Resum
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.