Journal
ORGANIC LETTERS
Volume 22, Issue 1, Pages 6-10Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b03527
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Funding
- Anhui Provincial Natural Science Foundation [1908085MB33]
- Anhui University of Technology
- Okinawa Institute of Science and Technology Graduate University
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Direct asymmetric synthesis of delta-hydroxy-beta-ketoesters was accomplished via regio- and enantioselective aldol reactions of beta-ketoesters with isatins catalyzed by cinchona alkaloid thiourea derivatives. The C-C bond formation of the reactions occurred only at the gamma-position of the beta-ketoesters. Reaction progress monitoring and product stability analyses under the conditions that included the catalyst indicated that the gamma-position reaction products were formed kinetically. Various delta-hydroxy-beta-ketoesters bearing 3-alkyl-3-hydroxyoxindole cores relevant to the development of bioactive molecules were synthesized.
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