Journal
TETRAHEDRON
Volume 58, Issue 41, Pages 8237-8246Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(02)00973-0
Keywords
Mukaiyama aldol reaction; asymmetric polymerization; chiral polymer; oxazaborolidinone; chiral derivatizing agent
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Asymmetric aldol polymerization of bis(triethylsilyl enol ether) and dialdehyde was performed in the presence of chiral N-sulfonyloxazaborolidinone as a catalyst. The polymerization occurred smoothly at low temperature (-78degreesC to -20degreesC) to afford optically active polymers having unique main-chain structure of beta-hydroxy carbonyl repeating unit. In order to estimate the asymmetric induction during the polymerization, asymmetric aldol reaction of triethylsilyl enol ether and benzaldehyde was studied as a model reaction. Optical purity of the chiral polymers obtained from the asymmetric polymerization was determined by using H-1 NMR analysis after their chiral derivatization with (R)-O-acetylmandelic acid. (C) 2002 Elsevier Science Ltd. All rights reserved.
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