Journal
SYNLETT
Volume 25, Issue 10, Pages 1461-1465Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0033-1341281
Keywords
tertiary alcohol; primary amine; organofluorine; organocatalysis; cross-aldol reaction
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Funding
- National Natural Science Foundation of China (NSFC) [21173064]
- Zhejiang Provincial Natural Science Foundation of China [LR14B0300001, LQ12B02004]
- Hangzhou Science and Technology Program [20130533B15, 20130432B06]
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It was found that the cinchona-derived primary amines and their combined catalyst systems with chiral organic acid or Lewis acid have been successfully applied in the cross-aldol reaction of trifluoromethyl ketones and aliphatic ketones. Excellent yields and good enantioselectivities (up to 89% ee) of the resulting beta-trifluoromethyl-beta-hydroxy ketones were obtained in the chiral primary amine catalyzed cross-aldol reaction under different conditions, which also led to both enantiomers of the desired products. This study also demonstrated the importance of synergistic effect of chiral organic acid on the primary amine catalysis.
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