Journal
REACTIVE & FUNCTIONAL POLYMERS
Volume 71, Issue 10, Pages 1055-1058Publisher
ELSEVIER SCIENCE BV
DOI: 10.1016/j.reactfunctpolym.2011.07.010
Keywords
Amylose; Asymmetric catalysis; Organocatalysis; Polysaccharide; Pyridine N-oxides
Funding
- Ministry of Education, Culture, Sports, Science, and Technology of Japan [21750120]
- Foundation for the Promotion of Ion Engineering
- Grants-in-Aid for Scientific Research [21750120] Funding Source: KAKEN
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Novel arnylose and cellulose derivatives bearing pyridine N-oxide groups were synthesized, and their performance as asymmetric organocatalysts was investigated. The amylose derivatives bearing 3-pyridyl N-oxide groups enantioselectively catalyzed the allylation of benzaldehyde by allyltrichlorosilane with different enantiomeric excesses (ee; 13-32% ee), depending on the degree of substitution of the pyridine N-oxide. In contrast, the corresponding cellulose derivatives showed the opposite enantioselectivity with much lower ee (2-11% ee). These results suggest that the higher-order structures of polysaccharides play an important role in the enantioselective allylation of benzaldehyde. (C) 2011 Elsevier Ltd. All rights reserved.
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