Utilizing the high dielectric constant of water: efficient synthesis of amino acid-derivatized cyclobutenones

Jun Li; Yongbin Han; Teresa B. Freedman; Shifa Zhu; Deborah J. Kerwood; Yan Yeung Luk

doi:10.1016/j.tetlet.2008.01.121

Utilizing the high dielectric constant of water: efficient synthesis of amino acid-derivatized cyclobutenones

Jun Li, Yongbin Han, Teresa B. Freedman, Shifa Zhu, Deborah J. Kerwood, Yan Yeung Luk

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

8 Scopus citations

Abstract

This work reports the use of water as a solvent to facilitate an efficient syntheses of amino acid-derivatized cyclobutenone. Kinetics studies in different solvents reveals that high dielectric constants of the solvents are the primary attribute for the high yielding and fast rate for this reaction. This class of substitution reactions in water also proceeds efficiently with a wide range of amino acids.

Original language	English (US)
Pages (from-to)	2128-2131
Number of pages	4
Journal	Tetrahedron Letters
Volume	49
Issue number	13
DOIs	https://doi.org/10.1016/j.tetlet.2008.01.121
State	Published - Mar 24 2008

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Utilizing the high dielectric constant of water: efficient synthesis of amino acid-derivatized cyclobutenones",

abstract = "This work reports the use of water as a solvent to facilitate an efficient syntheses of amino acid-derivatized cyclobutenone. Kinetics studies in different solvents reveals that high dielectric constants of the solvents are the primary attribute for the high yielding and fast rate for this reaction. This class of substitution reactions in water also proceeds efficiently with a wide range of amino acids.",

author = "Jun Li and Yongbin Han and Freedman, {Teresa B.} and Shifa Zhu and Kerwood, {Deborah J.} and Luk, {Yan Yeung}",

note = "Funding Information: We thank the Chemistry Department of SU, Syracuse Center for Excellence CARTI award supported by US Environmental Protection Agency [Grant Nos.: X-83232501-0] and NSF-CMMI [Grant No: 0727491] for financial support. We also thank Professor Boddy and Sponsler for helpful discussion. ",

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doi = "10.1016/j.tetlet.2008.01.121",

language = "English (US)",

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T1 - Utilizing the high dielectric constant of water

T2 - efficient synthesis of amino acid-derivatized cyclobutenones

AU - Li, Jun

AU - Han, Yongbin

AU - Freedman, Teresa B.

AU - Zhu, Shifa

AU - Kerwood, Deborah J.

AU - Luk, Yan Yeung

N1 - Funding Information: We thank the Chemistry Department of SU, Syracuse Center for Excellence CARTI award supported by US Environmental Protection Agency [Grant Nos.: X-83232501-0] and NSF-CMMI [Grant No: 0727491] for financial support. We also thank Professor Boddy and Sponsler for helpful discussion.

PY - 2008/3/24

Y1 - 2008/3/24

N2 - This work reports the use of water as a solvent to facilitate an efficient syntheses of amino acid-derivatized cyclobutenone. Kinetics studies in different solvents reveals that high dielectric constants of the solvents are the primary attribute for the high yielding and fast rate for this reaction. This class of substitution reactions in water also proceeds efficiently with a wide range of amino acids.

AB - This work reports the use of water as a solvent to facilitate an efficient syntheses of amino acid-derivatized cyclobutenone. Kinetics studies in different solvents reveals that high dielectric constants of the solvents are the primary attribute for the high yielding and fast rate for this reaction. This class of substitution reactions in water also proceeds efficiently with a wide range of amino acids.

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DO - 10.1016/j.tetlet.2008.01.121

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

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