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

doi:10.1021/ol101433v

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

Chemistry

Research output: Contribution to journal › Article › peer-review

34 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 language	English (US)
Pages (from-to)	3560-3563
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	15
DOIs	https://doi.org/10.1021/ol101433v
State	Published - Aug 6 2010

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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

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.",

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year = "2010",

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doi = "10.1021/ol101433v",

language = "English (US)",

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T1 - Facile procedure for generating side chain functionalized poly(α-hydroxy acid) copolymers from aldehydes via a versatile passerini-type condensation

AU - Rubinshtein, Mark

AU - James, Carrie R.

AU - Young, Jennifer L.

AU - Ma, Yanyan J.

AU - Kobayashi, Yoshihisa

AU - Gianneschi, Nathan C.

AU - Yang, Jerry

PY - 2010/8/6

Y1 - 2010/8/6

N2 - (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.

AB - (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.

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

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