Asymmetric syntheses of (2R,3R) and (2R,3S)-3-hydroxypipecolic acids are reported featuring a key diastereoselective addition of Büchi's Grignard reagent to the chiral serinal Image -5. Based on conformational analysis, a stereocontrolled reduction of piperidin-3-one (15) to cis 2,3-disubstituted piperidine (16) is also described.