Formal Synthesis of (+)-α-Conhydrine and Stereoselective Synthesis of Pyrrolidine Analogue via the Diastereoselective Chelation-Controlled Hydride Reduction and Wittig Reaction

Asymmetric syntheses of (+)-α-conhydrine and its pyrrolidine analogue were achieved from readily available L-serine. The key step involved highly diastereoselective chelation-controlled hydride reduction of the amino ketone to give the anti-amino alcohol and Wittig reaction.