Direct access to the optically active VAChT inhibitor vesamicol and its analogues via the asymmetric aminolysis of meso-epoxides with secondary aliphatic amines.
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.
Indian Institute of Technology Roorkee, Roorkee 247667, Uttarakhand, India. ramakpeddinti@gmail.com rkpdfcy@iitr.ac.in.
Arun
A
Sharma
Indian Institute of Technology Roorkee, Roorkee 247667, Uttarakhand, India. ramakpeddinti@gmail.com rkpdfcy@iitr.ac.in.
Jyoti
J
Agarwal
Indian Institute of Technology Roorkee, Roorkee 247667, Uttarakhand, India. ramakpeddinti@gmail.com rkpdfcy@iitr.ac.in.
Rama Krishna
http://orcid.org/0000-0001-7340-1516
RK
Peddinti
D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D003035:Cobalt / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry*; D015394:Molecular Structure; D055620:Optical Phenomena; D009942:Organometallic Compounds / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000588:Amines; D004852:Epoxy Compounds; D009942:Organometallic Compounds; D010880:Piperidines; C006189:vesamicol; D003035:Cobalt