Reaction of N-trityl amino acids with BOP: Efficient synthesis of t-butyl esters as well as N-trityl serine-and threonine-β-lactones

KM Sliedregt, A Schouten, J Kroon, RMJ Liskamp

Index: Sliedregt, Karen M.; Schouten, Arie; Kroon, Jan; Liskamp, Rob M.J. Tetrahedron Letters, 1996 , vol. 37, # 24 p. 4237 - 4240

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Citation Number: 32

Abstract

Upon exposure to methoxymethylamine and BOP, the stable hydroxybenzotriazolyl amide of TrPheOH was isolated instead of the expected Weinreb amide. This amide behaves as an active amide similar to the Weinreb amide and could be used, among others, for the synthesis of t-Bu esters. Reaction of N-trityl serine and threonine led to the corresponding β- lactones in unprecedented high yields.