Document Detail


Synthesis of functional poly(phenyl isocyanide)s with macromolecular helicity memory and their use as asymmetric organocatalysts.
MedLine Citation:
PMID:  18613092     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
To develop a novel polymer-based asymmetric organocatalyst, a series of helical poly(phenyl isocyanide)s with functional pendant groups were prepared by modifying the side groups of the optically active helical poly(4-carboxyphenyl isocyanide) with a macromolecular helicity memory. Helical polyisocyanides partially modified with achiral amines, such as piperazine, maintained their chiral memory and enantioselectively catalyzed a direct aldol reaction. Although the enantioselectivity was low, the original helical poly(4-carboxyphenyl isocyanide) showed no catalytic activity. These results indicated that the macromolecular helicity of the modified polyisocyanides together with bifunctional amino and carboxy acid pendant residues arranged in a helical array along the polymer backbones plays an important role in the enantioselectivity.
Authors:
Toshitaka Miyabe; Yoko Hase; Hiroki Iida; Katsuhiro Maeda; Eiji Yashima
Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Chirality     Volume:  21     ISSN:  1520-636X     ISO Abbreviation:  Chirality     Publication Date:  2009 Jan 
Date Detail:
Created Date:  2008-12-29     Completed Date:  2009-02-13     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  8914261     Medline TA:  Chirality     Country:  United States    
Other Details:
Languages:  eng     Pagination:  44-50     Citation Subset:  -    
Copyright Information:
(c) 2008 Wiley-Liss, Inc.
Affiliation:
Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya, Japan.
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