Journal
REACTIVE & FUNCTIONAL POLYMERS
Volume 82, Issue -, Pages 52-57Publisher
ELSEVIER SCIENCE BV
DOI: 10.1016/j.reactfunctpolym.2014.06.001
Keywords
Amylose; Asymmetric reaction; Cellulose; Chiral auxiliary; Polysaccharides
Funding
- Japan Prize Foundation
- Takahashi Industrial and Economic Research Foundation
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Cellulose and amylose derivatives bearing bromobenzoate pendants were synthesized as chiral auxiliaries to create optically active biaryl compounds through Suzuki-Miyaura cross-coupling with naphthalen-1-ylboronic acids. The regioselectively substituted polysaccharide derivatives bearing 2-bromobenzoate pendants at the 6-position of the glucose unit exhibited higher diastereoselectivity than did the corresponding monosaccharide-based chiral auxiliary and the non-regioselectively substituted polysaccharide derivative bearing 2-bromobenzoates at the 2,3,6-positions. These results suggest that the chiral induction by the regioselectively substituted polysaccharide-based auxiliaries is mainly based on regular higher-order structures, such as one-handed helical structures. (C) 2014 Elsevier Ltd. All rights reserved.
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