Highly Diastereoselective Synthesis of Threo or Erythro Aminoalkyl Epoxides from α-Amino Acids

Article abstract of DOI:10.1021/jo00126a019

α-Chloro-α'-(dibenzylamino)methylketones 3 are synthesized in enantiomerically pure form starting from α-amino acids.Reduction of amino ketones 3 and further epoxidation affords threo aminoalkyl epoxides 6 with diastereoisomeric excess ranging between 94percent and 98percent.The synthesis of erythro amino epoxides 9 is also described by reaction of α-amino aldehydes 7 with in situ generated (halomethyl)lithium.Amino epoxides 9 were obtained with a diastereoisomeric excess ranging between 91percent and 98percent.