Diastereoselective Formal [3+3] Cascade Cyclization towards Fused 4-Fluoroalkylated 3,4-Dihydro-2H-pyrans via Copper Catalysis
Weigao Hu , Jiawen Yin , Zhiyong Li , Yin Gao , Xuran Liu , Shenting Zhang , Wenzhu Yu , Lanmei Chen , Jia Zheng
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (15) : 1806 -1812.
Diastereoselective Formal [3+3] Cascade Cyclization towards Fused 4-Fluoroalkylated 3,4-Dihydro-2H-pyrans via Copper Catalysis
The cycloaddition and annulation reactions offer a powerful method toward various important substituted 3,4-dihydro-2H-pyran architectures. Nevertheless, the transformation for preparing fused-polycyclic ones still remains challenging yet highly desirable until now. Herein, we report a novel formal [3+3] cascade cyclization reaction to provide lactam-fused 4-fluoroalkylated 3,4-dihydropyran skeletons bearing three contiguous tertiary carbon centers via copper catalysis. Of note, these annulations proceeded in an exclusively diastereoselective manner through successive inert C(sp2)-Cl and C(sp3)-H functionalization, which exhibited highly site-selectivity and stereoselectivity. Additionally, evaluations on biological activities of the obtained products revealed that several products display inhibitory activity against Siha and H1975 cancer cell lines.
Diastereoselectivity / Formal [3+3] cascade cyclization / Fused 4-fluoroalkylated 3,4-dihydro-2H-pyran / Copper catalysis / Nucleophilic substitution / Isomerization / Oxy-Michael addition / Biological activity
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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