ol0c00533_si_001.pdf (14.22 MB)
NHC-Catalyzed Cascade Reaction between β‑Methyl Enals and Dienones for Quick Construction of Complex Multicyclic Lactones
journal contribution
posted on 2020-03-19, 16:38 authored by Jun Sun, Jun Xu, Guihua Nie, Zhichao Jin, Yonggui Robin ChiA NHC-promoted
cascade reaction between β-methyl enal and dienone
is developed for quick access to multicyclic lactone molecules bearing
quaternary chiral carbon centers. Our study constitutes the first
1,6-addition of the acylazolium vinyl enolate γ-carbon via NHC
catalysis and provides rapid access to complex lactone molecules that
are otherwise difficult to prepare. The structurally sophisticated
lactone products bearing up to four fused ring structures are afforded
in up to quantitative yields with good to excellent enantioselectivities.