Abstract
A diastereo- and enantioselective approach to access chiral CF2-functionalized aziridines from difluorodiazoethyl phenyl sulfone (PhSO2CF2CHN2) and in situ-formed aldimines is described. This multicomponent reaction is enabled by a combined strong Brønsted acid catalytic platform consisting of a chiral disulfonimide and 2-carboxyphenylboronic acid. The optical purity of the obtained CF2-substituted aziridines could be further improved by a practical dissolution–filtration procedure.
Highlights
Chiral aziridines are prevalently found in natural products and artificially made bioactive molecules, receiving significant attention in the past decades [1-6]
As arylboronic acids have been harnessed to enhance the Brønsted acidity in asymmetric organocatalysis in combination with chiral diols or chiral aminoalcohols [40-44], we envisioned that the simultaneous use of arylboronic acids and chiral Brønsted acids may bring about a complementary catalytic platform
We turned our attention to chiral disulfonimides developed by List, which have been established as a unique type of stronger Brønsted acids [45]
Summary
Chiral aziridines are prevalently found in natural products and artificially made bioactive molecules, receiving significant attention in the past decades [1-6]. Catalytic asymmetric approaches to chiral CF3-functionalized aziridines have only been reported by Cahard in 2012, who utilized trifluorodiazoethane (CF3CHN2) As the nucleophile to react with aldimines catalyzed by chiral phosphoric acid (Scheme 1a) [26].
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