Chiral shift reagent for amino acids based on resonance-assisted hydrogen bonding

Jik Chin; Chan Kim Dong; Hae Jo Kim; Francis B. Panosyan; Mook Kim Kwan

doi:10.1021/ol049084x

Chiral shift reagent for amino acids based on resonance-assisted hydrogen bonding

Jik Chin, Chan Kim Dong, Hae Jo Kim, Francis B. Panosyan, Mook Kim Kwan

Department of Chemistry & Nanoscience

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

74 Scopus citations

Abstract

(Matrix Presented) A chiral aldehyde that forms resonance-assisted hydrogen bonded imines with amino acids has been developed. This hydrogen bond not only increases the equilibrium constant for imine formation but also provides a highly downfield-shifted NMR singlet for evaluating enantiomeric excess and absolute stereochemistry of amino acids.

Original language	English
Pages (from-to)	2591-2593
Number of pages	3
Journal	Organic Letters
Volume	6
Issue number	15
DOIs	https://doi.org/10.1021/ol049084x
State	Published - 22 Jul 2004

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@article{4e0936087676489fb177927b0a964824,

title = "Chiral shift reagent for amino acids based on resonance-assisted hydrogen bonding",

abstract = "(Matrix Presented) A chiral aldehyde that forms resonance-assisted hydrogen bonded imines with amino acids has been developed. This hydrogen bond not only increases the equilibrium constant for imine formation but also provides a highly downfield-shifted NMR singlet for evaluating enantiomeric excess and absolute stereochemistry of amino acids.",

author = "Jik Chin and Dong, \{Chan Kim\} and Kim, \{Hae Jo\} and Panosyan, \{Francis B.\} and Kwan, \{Mook Kim\}",

year = "2004",

month = jul,

day = "22",

doi = "10.1021/ol049084x",

language = "English",

volume = "6",

pages = "2591--2593",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "15",

}

TY - JOUR

T1 - Chiral shift reagent for amino acids based on resonance-assisted hydrogen bonding

AU - Chin, Jik

AU - Dong, Chan Kim

AU - Kim, Hae Jo

AU - Panosyan, Francis B.

AU - Kwan, Mook Kim

PY - 2004/7/22

Y1 - 2004/7/22

N2 - (Matrix Presented) A chiral aldehyde that forms resonance-assisted hydrogen bonded imines with amino acids has been developed. This hydrogen bond not only increases the equilibrium constant for imine formation but also provides a highly downfield-shifted NMR singlet for evaluating enantiomeric excess and absolute stereochemistry of amino acids.

AB - (Matrix Presented) A chiral aldehyde that forms resonance-assisted hydrogen bonded imines with amino acids has been developed. This hydrogen bond not only increases the equilibrium constant for imine formation but also provides a highly downfield-shifted NMR singlet for evaluating enantiomeric excess and absolute stereochemistry of amino acids.

UR - https://www.scopus.com/pages/publications/4043095002

U2 - 10.1021/ol049084x

DO - 10.1021/ol049084x

M3 - Article

C2 - 15255698

AN - SCOPUS:4043095002

SN - 1523-7060

VL - 6

SP - 2591

EP - 2593

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

Chiral shift reagent for amino acids based on resonance-assisted hydrogen bonding

Abstract

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