Direct Generation of Ti-Enolate of α-CF3 Ketone:  Theoretical Study and High-Yielding and Diastereoselective Aldol Reaction

Y Itoh, M Yamanaka, K Mikami - Journal of the American Chemical …, 2004 - ACS Publications
Y Itoh, M Yamanaka, K Mikami
Journal of the American Chemical Society, 2004ACS Publications
… Facile defluorination is always an obstacle in the generation of α-CF 3 enolate. We
herein report our discovery of efficient generation of Ti-enolate directly from α-CF 3 ketone
and highly diastereoselective aldol reaction. … In conclusion, we have discovered that the Ti-enolate
of α-CF 3 ketone could be easily generated and that subsequent aldol reaction proceeds in
up to quantitative yield and virtually perfect diastereoselectivity. …
Success in the direct generation of the Ti-enolate of α-CF3 ketone and its aldol reaction is reported. The importance of Ti−F interaction during the course of the reaction is also reported.
ACS Publications
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