Stereocontrolled ring-opening of a hindered sulfamidate with nitrogen-containing aromatic heterocycles: synthesis of chiral quaternary imidazole derivatives |
| |
Authors: | Mata Lara Jiménez-Osés Gonzalo Avenoza Alberto Busto Jesús H Peregrina Jesús M |
| |
Institution: | Departamento de Qui?mica, Universidad de La Rioja, Centro de Investigacio?n en Si?ntesis Qui?mica, UA-CSIC, E-26006 Logron?o, Spain. |
| |
Abstract: | 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 (β(2,2)-amino acid). |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|