High Diastereoselective Synthesis of Threo or Erythro Aminoalkyl Epoxides from. alpha.-Amino Acids

J Barluenga, B Baragana…

Index: Barluenga, Jose; Baragana, Beatriz; Concellon, Jose M. Journal of Organic Chemistry, 1995 , vol. 60, # 21 p. 6696 - 6699

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Citation Number: 108

Abstract

a-Chloro-a'-(dibenzylamino) methylketones 3 are synthesized in enantiomerically pure form starting from a-amino acids. Reduction of amino ketones 3 and further epoxidation affords threo aminoalkyl epoxides 6 with diastereoisomeric excess ranging between 94% and 98%. The synthesis of erythro amino epoxides 9 is also described by reaction of a-amino aldehydes 7 with in situ generated (halomethy1) lithium. Amino epoxides 9 were obtained ...