The Journal of Organic Chemistry

Reactions of. alpha.-hydroxy carbonyl compounds with azodicarboxylates and triphenylphosphine: synthesis of. alpha.-N-hydroxy amino acid derivatives

T Kolasa, MJ Miller

Index: Kolasa, Teodozyj; Miller, Marvin J. Journal of Organic Chemistry, 1987 , vol. 52, # 22 p. 4978 - 4984

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Citation Number: 81

Abstract

Reaction of aliphatic a-hydroxy esters with azodicarboxylates and triphenylphosphine in the presence of either CbzNHOCHzPh or trOCNHOCH, Ph provides a direct route to protected aN-hydroxy amino acids. Similar reactions with aromatic a-hydroxy carbonyl compounds and derivatives result in predominate oxidation to the corresponding a-oxo carbonyl derivatives.