Abstract
A cinchona alkaloid-catalyzed enantioselective method has been developed for the synthesis of densely functionalized cyclohexanone derivatives with excellent diastereoselectivities and good enantioselectivities [diastereomeric ratio (dr) >95:5 and an enantiomeric excess (ee) value up to 86%]. The products have an all-carbon quaternary center that contains both a cyano and ester group flanked by two vicinal tertiary stereocenters. By using a one-pot procedure, the tautomeric products were then transformed into the corresponding pyrazoles, which were obtained as single isomers in good yields. A quinine-catalyzed enantioselective method has been reported to generate polysubstituted cyclohexenes that have an all-carbon quaternary center. The resulting isomeric product mixtures were easily converted into the corresponding pyrazoles through a one-pot procedure.
Original language | English |
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Pages (from-to) | 5254-5265 |
Number of pages | 12 |
Journal | European Journal of Organic Chemistry |
Volume | 2015 |
Issue number | 23 |
DOIs | |
Publication status | Published - 2015 Aug 1 |
Keywords
- Asymmetric synthesis
- Carbocycles
- Domino reactions
- Enones
- Michael addition
- Organocatalysis
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry