N-arylcarbonylpseudoprolines as tunable chiral derivatizing agents for the determination of the absolute configuration of secondary alcohols

So Yeong Han, Kihang Choi

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

New chiral derivatizing agents, 3-arylcarbonyl-2,2-dimethyloxazolidine-4- carboxylic acids (N-arylcarbonylpseudoprolines), were prepared through a simple, short-step synthesis. The absolute configuration of secondary alcohols can be assigned on the basis of the NMR spectroscopic chemical shift difference between diastereomeric pseudoproline esters. Preparation of more efficient agents was achieved simply by using aromatic groups with stronger anisotropic effect. New chiral derivatizing agents, N-arylcarbonylpseudoprolines, were prepared and used to determine the absolute configuration of secondary alcohols. Preparation of more efficient agents was achieved simply by using aromatic groups with stronger anisotropic effect.

Original languageEnglish
Pages (from-to)2920-2923
Number of pages4
JournalEuropean Journal of Organic Chemistry
Issue number16
DOIs
Publication statusPublished - 2011 Jun 1

Fingerprint

alcohols
Alcohols
configurations
preparation
Chemical shift
Carboxylic Acids
carboxylic acids
chemical equilibrium
esters
Esters
Nuclear magnetic resonance
nuclear magnetic resonance
synthesis

Keywords

  • Chirality
  • Configuration determination
  • Conformation analysis

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

Cite this

@article{d1a2ca01a9f44596aac370370472c703,
title = "N-arylcarbonylpseudoprolines as tunable chiral derivatizing agents for the determination of the absolute configuration of secondary alcohols",
abstract = "New chiral derivatizing agents, 3-arylcarbonyl-2,2-dimethyloxazolidine-4- carboxylic acids (N-arylcarbonylpseudoprolines), were prepared through a simple, short-step synthesis. The absolute configuration of secondary alcohols can be assigned on the basis of the NMR spectroscopic chemical shift difference between diastereomeric pseudoproline esters. Preparation of more efficient agents was achieved simply by using aromatic groups with stronger anisotropic effect. New chiral derivatizing agents, N-arylcarbonylpseudoprolines, were prepared and used to determine the absolute configuration of secondary alcohols. Preparation of more efficient agents was achieved simply by using aromatic groups with stronger anisotropic effect.",
keywords = "Chirality, Configuration determination, Conformation analysis",
author = "Han, {So Yeong} and Kihang Choi",
year = "2011",
month = "6",
day = "1",
doi = "10.1002/ejoc.201100209",
language = "English",
pages = "2920--2923",
journal = "Annalen der Pharmacie",
issn = "0075-4617",
publisher = "Wiley-VCH Verlag",
number = "16",

}

TY - JOUR

T1 - N-arylcarbonylpseudoprolines as tunable chiral derivatizing agents for the determination of the absolute configuration of secondary alcohols

AU - Han, So Yeong

AU - Choi, Kihang

PY - 2011/6/1

Y1 - 2011/6/1

N2 - New chiral derivatizing agents, 3-arylcarbonyl-2,2-dimethyloxazolidine-4- carboxylic acids (N-arylcarbonylpseudoprolines), were prepared through a simple, short-step synthesis. The absolute configuration of secondary alcohols can be assigned on the basis of the NMR spectroscopic chemical shift difference between diastereomeric pseudoproline esters. Preparation of more efficient agents was achieved simply by using aromatic groups with stronger anisotropic effect. New chiral derivatizing agents, N-arylcarbonylpseudoprolines, were prepared and used to determine the absolute configuration of secondary alcohols. Preparation of more efficient agents was achieved simply by using aromatic groups with stronger anisotropic effect.

AB - New chiral derivatizing agents, 3-arylcarbonyl-2,2-dimethyloxazolidine-4- carboxylic acids (N-arylcarbonylpseudoprolines), were prepared through a simple, short-step synthesis. The absolute configuration of secondary alcohols can be assigned on the basis of the NMR spectroscopic chemical shift difference between diastereomeric pseudoproline esters. Preparation of more efficient agents was achieved simply by using aromatic groups with stronger anisotropic effect. New chiral derivatizing agents, N-arylcarbonylpseudoprolines, were prepared and used to determine the absolute configuration of secondary alcohols. Preparation of more efficient agents was achieved simply by using aromatic groups with stronger anisotropic effect.

KW - Chirality

KW - Configuration determination

KW - Conformation analysis

UR - http://www.scopus.com/inward/record.url?scp=79956350065&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79956350065&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201100209

DO - 10.1002/ejoc.201100209

M3 - Article

SP - 2920

EP - 2923

JO - Annalen der Pharmacie

JF - Annalen der Pharmacie

SN - 0075-4617

IS - 16

ER -