Patent ID: 7439400

Claim:
A process for synthesizing a chiral compound having a formula of wherein Y is H, mono- or multi-substituted electron-withdrawing group or electron-donating group, and is located at m-, o-, or p-position of the benzene ring; P is hydrogen or an amino protecting group; Rf is a fluoro-containing alkyl; R is a trialkylsilyl, alkyl, cycloalkyl, or aryl group; R 6 is hydrogen and R 5 is hydroxy, or R 5 and R 6 are linked as —HNCO— to form a ring as in or its enantiomer, comprising the steps of (a) mixing a chiral ligand (1R,2R)-2-N,N— substituted-1-(substituted-phenyl)-2-R 3 -substituted-2-aminoethanol or its enantiomer having a formula of with a terminal alkyne and a Zn(II), Cu(II) or Cu(I) salt in the presence of an organic base in an aprotic solvent to form a mixture, wherein R 1 , R 2 is an amino protecting group; R 3 is an alkyl, alkyl-substituted with an alkyloxy or silyoxy, carboxylic group, carbalkoxy group, hydroxyl methyl, cycloalkyl, aryl, or CH 2 OR 4 , R 4 being an oxygen protecting group; Z is H, a mono- or multi-substituted electron-withdrawing group or electron-donating group, and located at m-, o-, or p-position of the benzene ring, and wherein the terminal alkyne is and R is a trialkylsilyl, alkyl, cycloalkyl, or aryl group, (b) mixing the mixture with a reactant having a formula of wherein P is hydrogen or an amino protecting group, Rf is a fluoro-containing alkyl, Y is H, a mono- or multi-subsubstituted electron-withdrawing group or electron-donating group and located at m-, o-, or p-positon of the ring, and (c) isolating and obtaining the chiral compound.