124288-95-5Relevant academic research and scientific papers
Highly efficient, enantioselective syntheses of (S)-(+)- and (R)-(-)-dapoxetine starting with 3-phenyl-1-propanol
Kang, Soyeong,Lee, Hyeon-Kyu
supporting information; experimental part, p. 237 - 240 (2010/04/06)
(Chemical Equation Presented) 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-Hamination 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.
A chiral rhodium carboxamidate catalyst for enantioselective C-H amination
Zalatan, David N.,Du Bois
supporting information; experimental part, p. 9220 - 9221 (2009/02/03)
Rh2(S-nap)4, a chiral dirhodium tetracarboxamidate complex, has been developed and shown to be an effective catalyst for the asymmetric, intramolecular C-H amination of sulfamate esters. Enantiomeric excesses range from 60-99% for a collection of disparately substituted 3-arylpropylsulfamates. In addition, Rh2(S-nap)4 is found to promote chemoselective allylic C-H oxidation of unsaturated sulfamates, a property not observed with other dirhodium complexes tested to date. Copyright
Stereoselective Synthesis and Absolute Stereochemistry of Sinefungin
Maguire, Martin P.,Feldman, Paul L.,Rapoport, Henry
, p. 948 - 955 (2007/10/02)
Sinefungin has been synthesized from D-ribose, L-ornithine, and adenine.L-Ornithine was converted to its δ-nitro analogue 10, which was coupled to the ribose derived aldehyde 11 by a potassium fluoride catalyzed nitro-aldol reaction.The resulting nitro al
