Author/Authors :
Xiao، نويسنده , , Dong and Lavey، نويسنده , , Brian J. and Palani، نويسنده , , Anandan and Wang، نويسنده , , Cheng and Aslanian، نويسنده , , Robert G. and Kozlowski، نويسنده , , Joseph A. and Shih، نويسنده , , Neng-Yang and McPhail، نويسنده , , Andrew T. and Randolph، نويسنده , , Gerard P. and Lachowicz، نويسنده , , Jean E. and Duffy، نويسنده , , Ruth A.، نويسنده ,
Abstract :
Unlike the lithiation of N-Boc-2-alkylpiperidines, which occurs at the 6-position, N-Boc-2-phenylpiperidine and N-Boc-2-phenylpyrrolidine can be lithiated exclusively at the 2-position. The tertiary carbanions can be trapped with a variety of electrophiles. This chemistry was used for the synthesis of a potent NK1 ligand (Ki = 0.3 nM). The bioactive configuration at the piperidine quaternary center was determined by X-ray analysis to be (S).
