Synthesis 2002(7): 0941-0944
DOI: 10.1055/s-2002-28502
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Synthesis of Chiral Polymers by Means of Repetitive Addition of Allylsilane to Aldehyde

Shinichi Itsuno*, Toshihiro Kumagai
Department of Materials Science, Toyohashi University of Technology, Toyohashi 441-8580, Japan
Fax: +81(532)446813; e-Mail: itsuno@tutms.tut.ac.jp;
Further Information

Publication History

Received 3 March 2002
Publication Date:
14 May 2002 (online)

Abstract

Monomers having both allyltrimethylsilyl and formyl groups were prepared. Chiral (acyloxy)borane initiated the repetitive polyaddition of the monomers to give optically active polymers having main chain configurational chirality. Optical purity of the chiral polymer was evaluated by the analysis of the degradation product.

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Benzaldehyde reacted with 1 equiv of methallyltrimethylsilane in the presence of 2 mol% of Sc(OTf)3 at r.t. Quantitative conversion was attained when propionitrile was used as solvent. Although MeCN and nitromethane gave high conversion, other solvents such as CH2Cl2, DMF, toluene, nitroethane gave no product. THF was polymerized in the presence of Sc(OTf)3.