Journal
ORGANIC LETTERS
Volume 17, Issue 20, Pages 5036-5039Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b02514
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A general organocatalytic asymmetric dehydrated Mannich reaction of fluoroalkyl hemiaminals with ketones is reported. In this Mannich reaction, previously less explored aryl ketones showed great reactivity. By virtue of this efficient method, a wide range of biologically active beta-amino ketones were directly obtained. More importantly, two different intermediates involved in the reaction were detected and identified by F-19 NMR and HRMS analysis. Furthermore, the synthetic utility of the products was demonstrated by the synthesis of the biologically active fluoroalkyl beta-amino alcohols.
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