A novel one-pot procedure for the stereoselective synthesis of alpha-hydroxy esters from ortho esters.

A novel one-pot procedure for the stereoselective synthesis of alpha-hydroxy esters from ortho esters was developed. Key steps were multi-heteroatom Cope rearrangements of O-acylated N-hydroxy-l-tert-leucinol-derived oxazoline N-oxides leading to alpha-acyloxy oxazolines and, after methanolysis, to the target molecules in 67-80% yield and 94-98% ee.