%0 Journal Article %A Kang, Soyeong %A Lee, Hyeon-Kyu %D 2010 %T Highly Efficient, Enantioselective Syntheses of (S)-(+)- and (R)-(−)-Dapoxetine Starting with 3-Phenyl-1-propanol %U https://acs.figshare.com/articles/journal_contribution/Highly_Efficient_Enantioselective_Syntheses_of_i_S_i_and_i_R_i__Dapoxetine_Starting_with_3_Phenyl_1_propanol/2803009 %R 10.1021/jo902176s.s002 %2 https://ndownloader.figshare.com/files/4497418 %K Enantioselective %K sequence %K Efficient %K prochiral %K esters %K research %K complex %K Rh %K enantioselective %K configuration %K Phenyl %K sulfamate %K intermediacy %K enantiomer %K dioxide %K pathway %K synthesis %K Du Bois %K catalyst %K chiral %K Synthese %K dirhodium %K pheny %K amination %X 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 Rh2(S-nap)4 catalyst, is determined to be R and not S as was originally reported. %I ACS Publications