Yb(OTf)3-Catalyzed Asymmetric [3+3] Cycloaddition of N-Vinyl Nitrones with Activated Cyclopropanes to Prepare 1, 2-Oxazines
Yu-Zheng Wu , Yue Leng , Yi-Xin Chen , Shi-Qiu Huang , Ning Zou , Chun-Hua Chen , Dong-Liang Mo
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (4) : 417 -422.
Yb(OTf)3-Catalyzed Asymmetric [3+3] Cycloaddition of N-Vinyl Nitrones with Activated Cyclopropanes to Prepare 1, 2-Oxazines
We described a Yb(OTf) 3 combined with Pybox ligand catalyzed asymmetric [3+3] cycloaddition of N-vinyl cinnamaldehyde nitrones with activated cyclopropanes to prepare various functionalized 1, 2-oxazines in 24%—95% yields and 22%—96% ee. Experimental results revealed that the reaction underwent a domino [3+3] cycloaddition, dealkenylation, and aza-1, 4-addition in three steps. The chiral 1, 2-oxazine could be obtained in gram scales and easily converted into various 1, 2-oxazine scaffolds. The present method features broad substrate scope, good functional group compatibility, three-component domino reaction, and asymmetric [3+3] cycloaddition of N-vinyl nitrones with activated cyclopropanes.
Cycloaddition / Cyclopropane / Nitrone / 1, 2-Oxazine |Asymmetric catalysis / Domino reactions / Michael addition / N-Heterocycle
2024 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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