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[3 + 2] Cycloaddition/Oxidative Aromatization Sequence via Photoredox Catalysis: One-Pot Synthesis of Oxazoles from 2H-Azirines and Aldehydes

Author:
Zeng, Ting-Ting, Xuan, Jun, Ding, Wei, Wang, Kuan, Lu, Liang-Qiu, Xiao, Wen-Jing
Source:
Organic letters 2015 v.17 no.16 pp. 4070-4073
ISSN:
1523-7052
Subject:
aldehydes, alkenes, catalytic activity, chemical structure, cycloaddition reactions, imines, oxazoles, prostaglandin synthase, redox reactions, synthesis
Abstract:
A novel [3 + 2] cycloaddition/oxidative aromatization sequence via visible light-induced photoredox catalysis is disclosed. It provides a general synthetic route to 2,4,5-trisubstituted oxazoles from easily accessible 2H-azirines and aldehydes under mild reaction conditions. The potential of this strategy was further demonstrated by the rapid synthesis of a cyclooxygenase-2 inhibitor as well as the success of employing electron-deficient alkenes and imines as the reaction partners.
Agid:
5789476