title: Facile procedure for generating side chain functionalized poly(alpha-hydroxy acid) copolymers from aldehydes via a versatile Passerini-type condensation.
abstract: 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.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093-0358, USA.
authors.forename: Mark
authors.initials: M
authors.lastname: Rubinshtein
authors.forename: Carrie R
authors.initials: CR
authors.lastname: James
authors.forename: Jennifer L
authors.initials: JL
authors.lastname: Young
authors.forename: Yanyan J
authors.initials: YJ
authors.lastname: Ma
authors.forename: Yoshihisa
authors.initials: Y
authors.lastname: Kobayashi
authors.forename: Nathan C
authors.initials: NC
authors.lastname: Gianneschi
authors.forename: Jerry
authors.initials: J
authors.lastname: Yang
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003300:Copper / Q000737:chemistry; D006880:Hydroxy Acids / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000447:Aldehydes; D006880:Hydroxy Acids; D007211:Indoles; D011108:Polymers; D003300:Copper