Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 19, Issue 21, Pages 4788-4795Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1ob00511a
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Funding
- University Key Research Projects of Henan Province [19A350009]
- Natural Science Foundation of Henan Province [202300410321]
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An efficient and enantioselective alpha-electrophilic difluoromethylation of beta-keto esters has been achieved by phase-transfer catalysis, providing good enantioselectivities and yields with high C/O regioselectivities. The C/O selectivity of beta-keto esters can be easily reversed and controlled, offering a novel and efficient way for introducing chiral C-CF2H groups.
An efficient and enantioselective alpha-electrophilic difluoromethylation of beta-keto esters has been achieved by phase-transfer catalysis. This procedure is applicable to different kinds of beta-keto esters with a series of cinchona-derived C-2 ' aryl-substituted phase-transfer catalysts. The reaction gives the corresponding products in good enantioselectivities (up to 83% ee) and yields (up to 92%) with high C/O regioselectivities (up to 98 : 2). Moreover, the C/O selectivity of beta-keto esters could be easily reversed and controlled. This asymmetric difluoromethylation provided a novel and efficient way for introducing chiral C-CF2H groups.
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