NHC-Catalyzed Cascade Reaction between β‑Methyl Enals and Dienones for Quick Construction of Complex Multicyclic Lactones

A 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 acces...

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Bibliographic Details
Published inOrganic letters Vol. 22; no. 7; pp. 2595 - 2599
Main Authors Sun, Jun, Xu, Jun, Nie, Guihua, Jin, Zhichao, Chi, Yonggui Robin
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.04.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
2-HYDROXYBENZOPHENONES
OXANDROLONE
CHROMONES
DIVERSE
DIELS-ALDER REACTION
ORGANOCATALYSIS
ALDEHYDES
DERIVATIVES
PROLINE
ASYMMETRIC ALDOL
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Summary:A 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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c00533