EMAIL THIS PAGE TO A FRIEND

The Journal of organic chemistry

Highly efficient, enantioselective syntheses of (S)-(+)- and (R)-(-)-dapoxetine starting with 3-phenyl-1-propanol.


PMID 19957926

Abstract

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.

Related Materials

Product #

Image

Description

Molecular Formula

Add to Cart

W288500
3-Phenyl-1-propanol, ≥98%, FCC
C9H12O
140856
3-Phenyl-1-propanol, 98%
C9H12O