Journal
CHEMICAL COMMUNICATIONS
Volume 52, Issue 44, Pages 7153-7156Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6cc02019d
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- Aarhus University
- Carlsberg Foundation
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Organocatalytic formed dienamines are shown to be involved in dynamic resolution of 2-cyclohexylidene acetaldehydes. By reaction of racemic 2-cyclohexylidene acetaldehydes with benzoquinones in the presence of a diarylprolinol-silyl ether catalyst, tricyclic products are formed in good to high yield and excellent enantioselectivity, while the diastereoselectivity depends on the substituent in the 2-cyclohexylidene acetaldehydes. Studies based on experimental observations and DFT-calculations point to a dynamic thermodynamic resolution-directed pathway. Some transformations of the optically active products are also presented.
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