Titanium-Catalyzed Stereoselective Geminal Heterodihalogenation of β-Ketoesters
- 15 April 2003
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 5 (10) , 1709-1712
- https://doi.org/10.1021/ol0343459
Abstract
β-Ketoesters can be effectively monofluorinated with F-TEDA using CpTiCl3 as a catalyst. With the use of this catalyst, the extent of the competing difluorination does not reach 10%. [TiCl2(TADDOLato)] complexes catalyze the one-pot enantioselective heterodihalogenation of β-ketoesters with F-TEDA and NCS to afford α-chloro-α-fluoro-β-ketoesters in moderate to good yields. The sequence of addition of the halogenating agents determines the sense of chiral induction.Keywords
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