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)

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