Synthesis of amides from unprotected amino acids by a simultaneous protection–activation strategy using dichlorodialkyl silanes

van Leeuwen, S.H., Quaedflieg, P.J.L.M., Broxterman, Q.B. and Liskamp, R.M.J. (2002) Synthesis of amides from unprotected amino acids by a simultaneous protection–activation strategy using dichlorodialkyl silanes. Tetrahedron Letters, 43(50), pp. 9203-9207. (doi: 10.1016/S0040-4039(02)02275-X)

Abstract

Reaction of l-phenylalanine (1) with dichlorodimethylsilane or other dichlorosilane derivatives 6b–d and primary amines leads to the formation of amides probably via a cyclic silyl intermediate. It is also possible to use β-amino acids and N-alkylated amino acids (peptoid building blocks) as well as the amino dicarboxylic acid l-aspartic acid. The latter leads to almost exclusive formation of the α-amide.

• 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., 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