10.1021/jo902176s.s001
Soyeong Kang
Soyeong
Kang
Hyeon-Kyu Lee
Hyeon-Kyu
Lee
Highly Efficient, Enantioselective Syntheses of (<i>S</i>)-(+)- and (<i>R</i>)-(−)-Dapoxetine Starting with 3-Phenyl-1-propanol
American Chemical Society
2010
Enantioselective
sequence
Efficient
prochiral
esters
research
complex
Rh
enantioselective
configuration
Phenyl
sulfamate
intermediacy
enantiomer
dioxide
pathway
synthesis
Du Bois
catalyst
chiral
Synthese
dirhodium
pheny
amination
2010-01-01 00:00:00
Dataset
https://acs.figshare.com/articles/dataset/Highly_Efficient_Enantioselective_Syntheses_of_i_S_i_and_i_R_i__Dapoxetine_Starting_with_3_Phenyl_1_propanol/2803012
A highly efficient, enantioselective sequence has been developed for the synthesis of (<i>S</i>)- and (<i>R</i>)-dapoxetine. The pathways involve the intermediacy of the 6-membered-ring sulfamate esters <b>4</b>, which were generated by Du Bois asymmetric C−H amination reactions of the prochiral sulfamate <b>3</b>, 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 (<b>4r</b>), prepared by the Du Bois asymmetric C−H amination reaction of <b>3</b> and the Rh<sub>2</sub>(<i>S</i>-nap)<sub>4</sub> catalyst, is determined to be <i>R</i> and not <i>S</i> as was originally reported.