Stereocontrolled Ring-Opening of a Hindered Sulfamidate with Nitrogen-Containing Aromatic Heterocycles: Synthesis of Chiral Quaternary Imidazole Derivates
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...
| Authors: | , , , , |
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| Format: | article |
| Status: | Published version |
| Publication Date: | 2011 |
| Country: | España |
| Institution: | Universidad de La Rioja (UR) |
| Repository: | RIUR. Repositorio Institucional de la Universidad de La Rioja |
| OAI Identifier: | oai:portal.dialnet.es:doc/5bbc6a1bb750603269e82723 |
| Online Access: | https://investigacion.unirioja.es/documentos/5bbc6a1bb750603269e82723 |
| Access Level: | Open access |
| Summary: | 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. |
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