期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2011, 期 1, 页码 62-65出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201001356
关键词
Ene reaction; Aldol reaction; Lewis acids; Palladium; Asymmetric catalysis
资金
- Japan Science and Technology Agency
Chiral dicationic Pd-complex-catalyzed enantioselective ene and aldol reactions with various isatin derivatives are shown to produce the corresponding 3-hydroxy-2-oxindole products in good yields with high enantioselectivities. These catalytic processes are effective not only with isatins but also with keto esters and diketones derivatives. Even with unprotected isatin, high yields and enantioselectivities were obtained to produce convolutamydine A as a naturally occurring compound. Sequentially, alpha-oxidation by m-CPBA and alpha-fluorination by selectfluor of the ene product could be achieved to give the corresponding alpha-hydroxy and alpha-fluoro ketones, respectively.
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