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The Selective O ‐Acylation of Hydroxyproline as a Convenient Method for the Large‐Scale Preparation of Novel Proline Polymers and Amphiphiles
Author(s) -
Kristensen Tor E.,
Hansen Finn K.,
Hansen Tore
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800941
Subject(s) - acylation , proline , chemistry , amphiphile , hydroxyproline , organic chemistry , trifluoroacetic anhydride , polymer , trifluoroacetic acid , combinatorial chemistry , amino acid , catalysis , biochemistry , copolymer
In this work we show how a direct O ‐acylation of trans ‐4‐hydroxy‐ L ‐proline with acyl chlorides in trifluoroacetic acid makes a range of novel proline derivatives readily available on large‐scale. No protecting groups or chromatographic techniques are involved in any of the procedures, and certain amphiphilic proline derivatives, which recently have received interest in synthesis, are now potentially some of the most readily accessible organocatalysts. The selective acylation was also utilized in the synthesis of a novel high‐load proline polymer, poly( O ‐acryloyl‐ trans ‐4‐hydroxy‐ L ‐proline), a polymer with the highest proline loading reported and for which classical methods failed for its preparation. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)