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

Sliedregt, K.M., Schouten, A., Kroon, J. and Liskamp, R.M.J. (1996) Reaction of N-trityl amino acids with BOP: Efficient synthesis of t-butyl esters as well as N-trityl serine- and threonine-β-lactones. Tetrahedron Letters, 37(24), pp. 4237-4240. (doi:10.1016/0040-4039(96)00805-2)

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Publisher's URL: http://dx.doi.org/10.1016/0040-4039(96)00805-2

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.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Liskamp, Professor Robert
Authors: Sliedregt, K.M., Schouten, A., Kroon, J., and Liskamp, R.M.J.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Tetrahedron Letters
ISSN:0040-4039

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