%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