Facile procedure for generating side chain functionalized poly(α-hydroxy acid) copolymers from aldehydes via a versatile passerini-type condensation

Mark Rubinshtein, Carrie R. James, Jennifer L. Young, Yanyan J. Ma, Yoshihisa Kobayashi, Nathan C. Gianneschi, Jerry Yang

Research output: Contribution to journalArticlepeer-review

32 Scopus citations

Abstract

(Equation Presented). A general method for synthesizing α-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(α-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(α-hydroxy acid) copolymers from readily available aldehydes, making it potentially useful as an approach to synthesize biodegradable polymers with new, tunable properties.

Original languageEnglish (US)
Pages (from-to)3560-3563
Number of pages4
JournalOrganic Letters
Volume12
Issue number15
DOIs
StatePublished - Aug 6 2010

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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