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J Org Chem. 2018 Feb 16;83(4):2263-2273. doi: 10.1021/acs.joc.7b03150. Epub 2018 Jan 30.

Enantioselective α-Benzoyloxylation of β-Keto Esters by N-Oxide Phase-Transfer Catalysts.

Author information

1
School of Pharmacy, Xinxiang Medical University , Xinxiang, 453003 Henan, People's Republic of China.
2
School of Pharmaceutical Science and Technology, Dalian University of Technology , Dalian, 116024 Liaoning, People's Republic of China.

Abstract

An efficient and enantioselective α-benzoyloxylation of β-keto esters has been achieved by phase-transfer catalysis. This simple catalytic procedure is applicable to a range of β-keto esters with cinchona-derived N-oxide asymmetric phase-transfer catalysts and gives the corresponding products in good enantiopurity (up to 95% ee) and yield (up to 99%). This simple and effective oxyfunctionalization is a useful synthetic strategy for introducing an oxygen-containing functional group at the α position of β-dicarbonyl compounds.

PMID:
29360355
DOI:
10.1021/acs.joc.7b03150

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