The synthesis of amides and dipeptides from unprotected amino acids by a simultaneous protection–activation strategy using boron trifluoride diethyl etherate

van Leeuwen, S.H., Quaedflieg, P.J.L.M., Broxterman, Q.B., Milhajlovic, Y. and Liskamp, R.M.J. (2005) The synthesis of amides and dipeptides from unprotected amino acids by a simultaneous protection–activation strategy using boron trifluoride diethyl etherate. Tetrahedron Letters, 46(4), pp. 653-656. (doi:10.1016/j.tetlet.2004.11.129)

Full text not currently available from Enlighten.

Abstract

The reaction of l-phenylalanine (1) with boron trifluoride diethyl etherate and primary amines leads to the formation of amides via a cyclic boron intermediate. It is also possible to use the amino dicarboxylic acid l-aspartic acid and N-alkylated amino acids (peptoid building blocks, e.g., NPhe-OH 9). The latter can be used in the preparation of dipeptidomimetics.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Liskamp, Professor Robert
Authors: van Leeuwen, S.H., Quaedflieg, P.J.L.M., Broxterman, Q.B., Milhajlovic, Y., and Liskamp, R.M.J.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Tetrahedron Letters
ISSN:0040-4039
ISSN (Online):1873-3581

University Staff: Request a correction | Enlighten Editors: Update this record