Enantioselective recognition of 1,2-amino alcohols by reversible formation of imines with resonance-assisted hydrogen bonds

Mook Kim Kwan; Hyunjung Park; Hae Jo Kim; Jik Chin; Wonwoo Nam

doi:10.1021/ol051267b

Enantioselective recognition of 1,2-amino alcohols by reversible formation of imines with resonance-assisted hydrogen bonds

Mook Kim Kwan, Hyunjung Park, Hae Jo Kim, Jik Chin, Wonwoo Nam

Department of Chemistry & Nanoscience

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

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Abstract

(Chemical Equation Presented) A chiral aldehyde with three H-bond donating groups (2) has been synthesized. This aldehyde binds a variety of chiral 1,2-amino alcohols in benzene with the same sense of stereoselectivity. Computational and experimental data indicate that one imine bond, one resonance-assisted H-bond to the imine nitrogen, and two H-bonds to the alcoholic oxygen all play an important role in the stereoselective recognition.

Original language	English
Pages (from-to)	3525-3527
Number of pages	3
Journal	Organic Letters
Volume	7
Issue number	16
DOIs	https://doi.org/10.1021/ol051267b
State	Published - 4 Aug 2005

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title = "Enantioselective recognition of 1,2-amino alcohols by reversible formation of imines with resonance-assisted hydrogen bonds",

abstract = "(Chemical Equation Presented) A chiral aldehyde with three H-bond donating groups (2) has been synthesized. This aldehyde binds a variety of chiral 1,2-amino alcohols in benzene with the same sense of stereoselectivity. Computational and experimental data indicate that one imine bond, one resonance-assisted H-bond to the imine nitrogen, and two H-bonds to the alcoholic oxygen all play an important role in the stereoselective recognition.",

author = "Kwan, {Mook Kim} and Hyunjung Park and Kim, {Hae Jo} and Jik Chin and Wonwoo Nam",

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T1 - Enantioselective recognition of 1,2-amino alcohols by reversible formation of imines with resonance-assisted hydrogen bonds

AU - Kwan, Mook Kim

AU - Park, Hyunjung

AU - Kim, Hae Jo

AU - Chin, Jik

AU - Nam, Wonwoo

PY - 2005/8/4

Y1 - 2005/8/4

N2 - (Chemical Equation Presented) A chiral aldehyde with three H-bond donating groups (2) has been synthesized. This aldehyde binds a variety of chiral 1,2-amino alcohols in benzene with the same sense of stereoselectivity. Computational and experimental data indicate that one imine bond, one resonance-assisted H-bond to the imine nitrogen, and two H-bonds to the alcoholic oxygen all play an important role in the stereoselective recognition.

AB - (Chemical Equation Presented) A chiral aldehyde with three H-bond donating groups (2) has been synthesized. This aldehyde binds a variety of chiral 1,2-amino alcohols in benzene with the same sense of stereoselectivity. Computational and experimental data indicate that one imine bond, one resonance-assisted H-bond to the imine nitrogen, and two H-bonds to the alcoholic oxygen all play an important role in the stereoselective recognition.

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ER -

Enantioselective recognition of 1,2-amino alcohols by reversible formation of imines with resonance-assisted hydrogen bonds

Abstract

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