BF3·Et2O and trifluoroacetic acid/triethyl amine-mediated synthesis of functionalized piperidines

A two-step short and efficient strategy for the synthesis of substituted piperidones and piperidines in high diastereoselectivity (only trans-configuration), by employing cascade type reaction using BF3·Et2O or by carrying out one pot deprotection of tBoc group followed by intramolecular aza-Michael addition of α,β-unsaturated beta keto esters has been developed. Using a similar strategy a short access to hydroxy pipecolic acid is also described. Very simple and rapid experimental procedures involving mild conditions and only one or two chromatographic purifications are the main features of the process.