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Polycondensation of α‐amino acid esters in the presence of yttrium triflate as a Lewis acid
Authors:Tadamasa Nemoto  Daisuke Ando  Kensuke Naka  Yoshiki Chujo
Abstract:To develop polycondensation methods for poly(α‐amino acid)s, we describe a first examination to use yttrium triflate as a Lewis acid for polycondensation of α‐amino acid esters. In the absence of Lewis acid, no polycondensation of 2‐methoxyphenyl glycinate ( 1b ) at room temperature proceeded. While the polycondensation of 1b was carried out with 5 mol % yttrium triflate, a condensation product of glycine was obtained in 16% yield. Although polycondensation of 4‐nitrophenyl L ‐leucinate ( 1c ) and 4‐nitrophenyl L ‐valinate ( 1d ) were also promoted with 5 mol % yttrium triflate, the condensation products of both α‐amino acid esters were obtained in only a few percent yield. When 1d was polymerized in the presence of 100 mol % yttrium triflate, high molecular weight poly(L ‐valine) was obtained in 91% yield. © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 44: 4731–4735, 2006
Keywords:α  ‐amino acid ester  lewis acid  poly(α  ‐amino acid)s  polycondensation  yttrium triflate
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