Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 5, Pages 4262-4273Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c00163
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Funding
- Leading Innovative and Entrepreneur Team Introduction Program of Zhejiang [2019R01005]
- Joint Fund of Zhejiang Provincial Natural Science Foundation [LTZ21B020001]
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An organocatalyzed cascade reaction was developed for the construction of axially chiral compounds with high yields and enantioselectivities. Further transformations of the synthesized products were explored to illustrate their synthetic applications.
An organocatalyzed cascade aza-Michael/Aldol reaction of alkynals with N-(2-(1-naphthoyl)phenyl)-benzenesulfonamides has been disclosed. In the presence of a secondary amine catalyst, this method enables the construction of a series of axially chiral 4-naphthylquinoline-3-carbaldehydes in yields of up to 97% with enantioselectivities of up to 96%. Several further transformations of the synthesized products were investigated to demonstrate their synthetic applications.
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