Highly Enantioselective Construction of Azaspiro[4.5]decane via an NHC-catalyzed [5+1] Cycloaddition
Jiahan Li , Xiao-Yong Duan , Yuxuan Feng , Peipei Xu , Zhongyu Yang , Zhihang Li , Jing Cao , Jing Qi
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (23) : 3178 -3182.
Azaspiro[4.5]decane scaffold represents a privileged structural motif that is widely found in natural products, bioactive molecules, and pharmaceuticals. Herein, we report the first N-heterocyclic carbene (NHC)-catalyzed [5+1] annulation of α,β-γ,δ-unsaturated aldehydes with 3-aminomaleimides for the efficient construction of azaspiro[4.5]decanes. This mechanistically distinct transformation proceeds under mild conditions to afford desired spirocyclic products in good yields (up to 85%) with excellent enantioselectivities (99% ee). Notably, this enantioselective catalysis demonstrates broad substrate compatibility, enabling efficient late-stage functionalization of structurally diverse pharmaceuticals and bioactive molecules.
Asymmetric catalysis / Enantioselectivity / Cycloaddition / NHC organocatalysis / [5+1] cycloaddition / Azaspiro[4.5]decane
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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