期刊
CHEMICAL SCIENCE
卷 4, 期 11, 页码 4146-4155出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3sc51791h
关键词
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资金
- Royal Society for a University Research Fellowships
- Carnegie Trust for the Universities of Scotland
- European Research Council under the European Union's Seventh Framework Programme (FP7/ERC) [279850]
- Engineering and Physical Sciences Research Council [GR/S31273/01] Funding Source: researchfish
HBTM-2.1 promotes the catalytic asymmetric intermolecular Michael-lactonisation of arylacetic acids and trifluoromethylenones in the presence of pivaloyl chloride, giving C(6)-trifluoromethyldihydropyranones with high diastereo- and enantiocontrol (up to 95 : 5 dr and >99% ee) that are readily derivatised to diverse synthetic building blocks containing trifluoromethyl-stereogenicity. Kinetic studies indicate the reaction is first order with respect to both in situ formed mixed anhydride and catalyst concentration, with a primary kinetic isotope effect observed using a, alpha,alpha-di-deuterio 4-fluorophenylacetic acid, consistent with rate determining deprotonation of an intermediate acyl isothiouronium ion.
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