Highly efficient, enantioselective syntheses of (S)-(+)- and (R)-(-)-dapoxetine starting with 3-phenyl-1-propanol.
A highly efficient, enantioselective sequence has been developed for the synthesis of (S)- and (R)-dapoxetine. The pathways involve the intermediacy of the 6-membered-ring sulfamate esters 4, which were generated by Du Bois asymmetric C-H amination reactions of the prochiral sulfamate 3, catalyzed by the chiral dirhodium(II) complexes. During the course of our research, the absolute configuration of the enantiomer of 4-pheny[1,2,3]oxathiazinane 2,2-dioxide (4r), prepared by the Du Bois asymmetric C-H amination reaction of 3 and the Rh(2)(S-nap)(4) catalyst, is determined to be R and not S as was originally reported.
Kang
Soyeong
S
Drug Discovery Division, Korea Research Institute of Chemical Technology, P.O. Box 107, Yuseong, Daejeon 305-600, Korea.
Lee
Hyeon-Kyu
HK
D001596:Benzylamines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D001596:Benzylamines; D009281:Naphthalenes; D020005:Propanols; C016655:3-phenylpropanol-1; C080598:dapoxetine