Abstract
Bifunctional chiral 2-aminobenzimidazole derivatives 1 and 2 catalyze the enantioselective stereodivergent α-chlorination of β-ketoesters and 1,3-diketone derivatives with up to 50% ee using N-chlorosuccinimide (NCS) or 2,3,4,4,5,6-hexachloro-2,5-cyclohexadien-1-one as electrophilic chlorine sources.
Highlights
IntroductionAbout 85 percent of all pharmaceuticals (prescription and over-the-counter) contain or are manufactured using chlorine
About 85 percent of all pharmaceuticals contain or are manufactured using chlorine
Due to the potential of these compounds, their catalytic asymmetric synthesis has been intensively investigated in the past few years [5,6,7]
Summary
About 85 percent of all pharmaceuticals (prescription and over-the-counter) contain or are manufactured using chlorine. In 2004, MacMillan [12], Lectka [13], and Jørgensen [14] reported the first catalytic highly enantioselective α-chlorination of aldehydes, acid chlorides, and ketones, respectively, using perchloroquinones and N-chlorosuccinimide (NCS) as chlorination reagents After these preliminary works, the enantioselective α-chlorination of ketones [15] and aldehydes [16,17,18,19,20] has remained under study, other derivatives such as 1,3-dicarbonyl compounds [21,22,23,24,25,26,27], oxindoles [28,29], and silyl ketene acetals [30], being recently added to the nucleophile pool of this transformation.
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