Journal
ORGANIC LETTERS
Volume 19, Issue 19, Pages 5336-5339Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b02628
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Funding
- Ministry of Science, ICT, and Future Planning in Korea [NRF-2014R1A2A1A01005794, NRF-2016R1A4A1011451]
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Biologically relevant chiral 3,3-disubstituted oxindole products containing alpha beta-fluoroamine unit are obtained in high yields and with excellent stereoselectivity (up to 99% ee, dr >20:1 for syn) through the organocatalytic direct Mannich reaction of 3-fluoro-oxindoles as fluoroenolate precursors and a-amidosulfones as the bench-stable precursors of sensitive imines by using a chiral oligoethylene glycol and KF as a cation-binding catalyst and base, respectively. This protocol can be easily scaled without compromising the asymmetric induction. Furthermore, this protocol was also successfully extended to generate tetrasubstituted C-Cl and C-Br stereogenic centers.
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