Direct access to the optically active VAChT inhibitor vesamicol and its analogues via the asymmetric aminolysis of meso-epoxides with secondary aliphatic amines.

Arun Sharma, Jyoti Agarwal, Rama Krishna Peddinti

Organic & biomolecular chemistry 2017 Feb 22

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First highly enantioselective synthesis of biologically important vesamicol, benzovesamicol, and their derivatives was achieved via the desymmetrization of meso-epoxides with secondary aliphatic amines (4-phenylpiperidine derivatives) using a chiral [salenCo(iii)-BF4] catalyst at room temperature. All products were obtained in good yield and with excellent optical induction.

Citation

Arun Sharma, Jyoti Agarwal, Rama Krishna Peddinti. Direct access to the optically active VAChT inhibitor vesamicol and its analogues via the asymmetric aminolysis of meso-epoxides with secondary aliphatic amines. Organic & biomolecular chemistry. 2017 Feb 22;15(8):1913-1920