Document Detail

Facile procedure for generating side chain functionalized poly(alpha-hydroxy acid) copolymers from aldehydes via a versatile Passerini-type condensation.
MedLine Citation:
PMID:  20608664     Owner:  NLM     Status:  MEDLINE    
A general method for synthesizing alpha-hydroxy N-acylindoles in one-pot via an acid-catalyzed condensation of a convertible isonitrile with water and various aldehydes is presented. These intermediates were incorporated into poly(alpha-hydroxy acid) copolymers bearing residues with functionalizable side chains, which could be further modified through Cu(I)-catalyzed azide-alkyne cylcoaddition reactions. This versatile synthetic strategy provides access to side chain functionalized poly(alpha-hydroxy acid) copolymers from readily available aldehydes, making it potentially useful as an approach to synthesize biodegradable polymers with new, tunable properties.
Mark Rubinshtein; Carrie R James; Jennifer L Young; Yanyan J Ma; Yoshihisa Kobayashi; Nathan C Gianneschi; Jerry Yang
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S.    
Journal Detail:
Title:  Organic letters     Volume:  12     ISSN:  1523-7052     ISO Abbreviation:  Org. Lett.     Publication Date:  2010 Aug 
Date Detail:
Created Date:  2010-07-30     Completed Date:  2010-11-02     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  United States    
Other Details:
Languages:  eng     Pagination:  3560-3     Citation Subset:  IM    
Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093-0358, USA.
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MeSH Terms
Aldehydes / chemistry*
Combinatorial Chemistry Techniques
Copper / chemistry
Hydroxy Acids / chemical synthesis*,  chemistry
Indoles / chemical synthesis,  chemistry
Molecular Structure
Polymers / chemical synthesis*,  chemistry
Reg. No./Substance:
0/Aldehydes; 0/Hydroxy Acids; 0/Indoles; 0/Polymers; 7440-50-8/Copper

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