Stereoselective Synthesis of δ- and ε-Amino Ketone Derivatives from <i>N</i>-<i>tert</i>-Butanesulfinyl Aldimines and Functionalized Organolithium Compounds

Abstract

The addition of functionalized organolithium compounds derived from 5-chloro-2-methoxy-1-pentene and 6-chloro-2-methoxy-1-hexene to N-tert-butanesulfinyl aldimines imines, and a subsequent hydrolysis of the enol ether moiety, yielded different δ- and ε-amino ketone derivatives, respectively, in moderate yields and diastereoselectivities. The application of these compounds in organic synthesis was demonstrated by the preparation of 2-substituted 6-methylpiperidines in a stereoselective manner, among them natural alkaloids (+)- and (−)-isosolenopsin A.

Keywords

• chiral sulfinyl imines
• functionalized organolithium compounds
• diastereoselective additions
• piperidine alkaloids
• isosolenopsin A