De novo Synthesis of Chiral 3, 4-Dihydroquinazolines via One-Pot Enantioselective Ugi-Azide/Cyclization Sequences
Zu-Kui Xie , Jun-Jun Ding , Yi-Ming Ou , Jun-Xiu Shi , Meng-Lan Shen , Chuan-Zhi Yao , Hua-Jie Jiang , Jie Yu
Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (18) : 2140 -2146.
De novo Synthesis of Chiral 3, 4-Dihydroquinazolines via One-Pot Enantioselective Ugi-Azide/Cyclization Sequences
Herein, we reported a precise de novo synthesis of chiral 3, 4-dihydroquinazoline frameworks via a one-pot anionic stereogenic-at-cobalt(III) complex-catalyzed enantioselective Ugi-azide/Pd-catalyzed cyclization sequence. This powerful protocol involves 5 components and 2 catalytic systems, delivering chiral 3, 4-dihydroquinazolines with excellent enantioselectivities (up to 94% ee). The preliminary antifungal experiments suggest that both Ugi-adducts and 3, 4-dihydroquinazolines have great potential in inhibiting plant pathogens such as Trichoderma viride and Fusarium graminearum.
Anionic stereogenic-at-cobalt(III) complex / De novo synthesis / post-Ugi transformation / One-pot sequence / Asymmetric synthesis / Multicomponent reactions
2024 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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