Facile Procedure for Generating Side Chain Functionalized Poly(α-hydroxy acid) Copolymers from Aldehydes via a Versatile Passerini-Type Condensation

• Published in: Organic letters Vol. 12; no. 15; pp. 3560 - 3563
• Main Authors: Rubinshtein, Mark, James, Carrie R, Young, Jennifer L, Ma, Yanyan J, Kobayashi, Yoshihisa, Gianneschi, Nathan C, Yang, Jerry
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 06.08.2010; Amer Chemical Soc
• Subjects: Aldehydes - chemistry; Catalysis; Chemistry; Chemistry, Organic; Combinatorial Chemistry Techniques; Copper - chemistry; Hydroxy Acids - chemical synthesis; Hydroxy Acids - chemistry; Indoles - chemical synthesis; Indoles - chemistry; Molecular Structure; Physical Sciences; Polymers - chemical synthesis; Polymers - chemistry; Science & Technology; SURGERY; CYCLOADDITION; PYROGLUTAMIC ACIDS; BIODEGRADABLE POLYMERS; DRUG-DELIVERY; DEGRADATION; UGI-REACTION
• ISSN: 1523-7060; 1523-7052
• DOI: 10.1021/ol101433v

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.