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Abstract
The reaction of α-chloroenamines 1 with an excess of lithium and a catalytic amount of 4,4’-ditert-butylbiphenyl (DTBB) in THF at –90 oC followed by reaction with an electrophile (D2O, Me3SiCl, PhCOCH=CHPh/BF3, CO2, CyNCO) and final hydrolysis gave the expected functionalized enamines 2. In the case of aldehydes (t-BuCHO, n-C5H11CHO, PhCHO) it was necessary to perform the lithiation in the presence of the electrophile (Barbier conditions) at – 40 oC. Hydrolysis of the obtained enamines either with silica gel or with hydrochloric acid yielded the expected functionalized ketones 3.
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