Highly selective difluoromethylations of β-keto amides with TMSCF2Br under mild conditions
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Without employing any transition metal and other additives, efficient methods for selective difluoromethylations of β-keto amides with TMSCF2Br reagent have been developed under alkaline and open-air conditions. This protocol allows a convenient access to various α-difluoromethyl β-keto amides with excellent yields (up to 93%) and high C/O regioselectivities (up to 99:1). The C/O selectivity of β-keto amides could be easily reversed and controlled by simply changing the base. This protocol can be easily scaled up and the C-difluoromethylation product could be reduced into amino-alcohol derivatives. Moreover, the first enantioselective electrophilic difluoromethylation of β-keto amides has been achieved by phase-transfer catalysis.
1984 ◽
Vol 49
(6)
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pp. 1138-1140
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2004 ◽
Vol 5
(5)
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pp. 259-263
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1980 ◽
Vol 333
(1 Transition Me)
◽
pp. 208-224
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