Chiral C1 symmetric imidazole-pyridine-imidazolinone tridentate nitrogen ligand as well as synthesis and application thereof

• Main Authors: YANG CHUN, WANG DONGCHAO, XIE MINGSHENG, QU GUIRONG, WU XIAOXIA, GUO HAIMING, XUE BAIYU, WANG HAIXIA
• Format: Patent
• Language: Chinese; English
• Published: 08.03.2024
• Subjects: APPARATUS THEREFOR; CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOIDCHEMISTRY; CHEMISTRY; GENERAL METHODS OF ORGANIC CHEMISTRY; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY; PERFORMING OPERATIONS; PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL; THEIR RELEVANT APPARATUS; TRANSPORTING

The invention discloses a chiral C1 symmetric imidazole-pyridine-imidazolinone tridentate nitrogen ligand as well as synthesis and application thereof, and belongs to the technical field of organic chemistry. The preparation method comprises the following steps: synthesizing a chiral C1 symmetric imidazole-pyridine-imidazolinone tridentate nitrogen ligand by taking cheap and easily available 2, 6-pyridylaldehyde, prolinamide and N-Ts phenylethylenediamine as raw materials; under the catalysis of Lewis acid and the ligand, aminocyclopropane and indole are subjected to asymmetric dearomatization [3 + 2] cycloaddition reaction, good chemical selectivity and excellent enantioselectivity are obtained, and the product contains three chiral carbons. 本发明公开了手性C1对称咪唑-吡啶-咪唑啉酮三齿氮配体及其合成和应用，属于有机化学技术领域。以廉价易得2,6-吡啶甲醛、脯氨酰胺及N-Ts苯基乙二胺为原料，合成了手性C1对称咪唑-吡啶-咪唑啉酮三齿氮配体；在路易斯酸和该类配体催化下，氨基环丙烷与吲哚不对称脱芳构化[3+2]环加成反应,取得了良好化学选择性和优异对映选择性，产物含有三个手性碳。