期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 8, 页码 2459-2463出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201814607
关键词
7-azaindolines; aldol reaction; asymmetric catalysis; C-C bond formation; fluorine
资金
- ACT-C from JST [JPMJCR12YO]
- KAKENHI from JSPS [17H03025, JP16H01043]
alpha-Oxygen-functionalized amides found particular utility as enolate surrogates for direct aldol couplings with alpha-fluorinated ketones in a catalytic manner. Because of the likely involvement of open transition states, both syn- and anti-aldol adducts can be accessed with high enantioselectivity by judicious choice of the chiral ligands. A broad variety of alkoxy substituents on the amides and aryl and fluoroalkyl groups on the ketone were tolerated, and the corresponding substrates delivered a range of enantioenriched fluorinated 1,2-dihydroxycarboxylic acid derivatives with divergent diastereoselectivity depending on the ligand used. The amide moiety of the aldol adduct was transformed into a variety of functional groups without protection of the tertiary alcohol, showcasing the synthetic utility of the present asymmetric aldol process.
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