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Asymmetric Polymer Synthesis by Repetitive Sakurai–Hosomi Allylation Reaction of Compounds Possessing Both Formyl and Allylsilane Functions
Author(s) -
Itsuno Shinichi,
Kumagai Toshihiro
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200210)85:10<3185::aid-hlca3185>3.0.co;2-b
Subject(s) - chemistry , lewis acids and bases , benzaldehyde , yield (engineering) , polymer , organic chemistry , methylene , asymmetric induction , degradation (telecommunications) , enantioselective synthesis , polymer chemistry , catalysis , materials science , metallurgy , telecommunications , computer science
Trialkylallylsilanes generally react with aldehydes in the presence of a Lewis acid to the corresponding homoallylic alcohols. Chiral Lewis acids promote the same reaction to yield the enantiomerically‐enriched homoallylalcohols. We have prepared four compounds ( 7 – 10 ) that possess both formyl and allylsilane functions. Lewis acids initiated self‐polyaddition reactions of these compounds by means of repetitive allylation. The use of chiral Lewis acids resulted in the formation of optically active polymers that possess exo ‐methylene and secondary OH functions in their main chain. The optical purity of these chiral polymers was estimated based on the results of model asymmetric reactions between benzaldehyde and β ‐substituted allylsilanes and by controlled degradation.