Efficient One‐Pot Synthesis of Enantiomerically Pure 2‐(Hydroxymethyl)morpholines

An efficient and convenient one‐pot procedure for the synthesis of enantiomerically pure 2‐(hydroxymethyl)morpholines with a widely variable substitution pattern was developed. Addition of chiral β‐amino alcohols to (S)‐ or (R)‐epichlorohydrin in the presence of LiClO4 afforded the corresponding chloro alcohols, which were treated with NaOMe to give the epoxides and, by subsequent intramolecular cyclization, the target compounds in good yields (57–77 %). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)