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

✍ Scribed by S.H. van Leeuwen; P.J.L.M. Quaedflieg; Q.B. Broxterman; R.M.J. Liskamp

Book ID: 104252432
Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 155 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)02275-x

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✦ Synopsis

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 b-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 a-amide.

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