Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 21, Pages 9601-9608Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo3016242
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Funding
- National Natural Science Foundation of China [21176041]
- State Key Laboratory of Fine Chemicals
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Cinchona alkaloid-derived chiral quaternary ammonium organocatalysts were developed. The catalyst with a bulky 1-adamantoyl group at the C-9 position promoted the enantioselective alpha-hydroxylation of beta-oxo esters and resulted in the corresponding products in 35-95% yields and 58-90% ee. The reaction was successfully scaled to a gram-quantity scale with a similar yield without loss of enantioselectivity.
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