Kinetic resolution of racemic carboxylic acids by an L-histidine-derived sulfonamide-induced enantioselective esterification reaction

Kazuaki Ishihara, Yuji Kosugi, Shuhei Umemura, Akira Sakakura

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

(Chemical Equation Presented) The direct and catalytic kinetic resolution of racemic carboxylic acids bearing a Brønsted base such as O-protected α-hydroxy carboxylic acids and N-protected α-amino acids has been accomplished through an L-histidine-derived sulfonamide-induced enantioselective esterification reaction with tert-butyl alcohol for the first time. Highly asymmetric induction [S(kfast/kslow) = up to 56] has been achieved under the equilibrium between a chiral catalyst and two diastereomeric acylammonium salts through an intramolecular hydrogen-bonding interaction.

Original languageEnglish
Pages (from-to)3191-3194
Number of pages4
JournalOrganic Letters
Volume10
Issue number15
DOIs
Publication statusPublished - 2008
Externally publishedYes

Fingerprint

histidine
Esterification
Sulfonamides
Carboxylic Acids
Histidine
carboxylic acids
Bearings (structural)
tert-Butyl Alcohol
Hydroxy Acids
Kinetics
kinetics
Hydrogen Bonding
amino acids
induction
Hydrogen bonds
alcohols
Salts
salts
Amino Acids
catalysts

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Kinetic resolution of racemic carboxylic acids by an L-histidine-derived sulfonamide-induced enantioselective esterification reaction. / Ishihara, Kazuaki; Kosugi, Yuji; Umemura, Shuhei; Sakakura, Akira.

In: Organic Letters, Vol. 10, No. 15, 2008, p. 3191-3194.

Research output: Contribution to journalArticle

@article{3550bf1ba8b44992b431d4e60ba32bd3,
title = "Kinetic resolution of racemic carboxylic acids by an L-histidine-derived sulfonamide-induced enantioselective esterification reaction",
abstract = "(Chemical Equation Presented) The direct and catalytic kinetic resolution of racemic carboxylic acids bearing a Br{\o}nsted base such as O-protected α-hydroxy carboxylic acids and N-protected α-amino acids has been accomplished through an L-histidine-derived sulfonamide-induced enantioselective esterification reaction with tert-butyl alcohol for the first time. Highly asymmetric induction [S(kfast/kslow) = up to 56] has been achieved under the equilibrium between a chiral catalyst and two diastereomeric acylammonium salts through an intramolecular hydrogen-bonding interaction.",
author = "Kazuaki Ishihara and Yuji Kosugi and Shuhei Umemura and Akira Sakakura",
year = "2008",
doi = "10.1021/ol801007m",
language = "English",
volume = "10",
pages = "3191--3194",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "15",

}

TY - JOUR

T1 - Kinetic resolution of racemic carboxylic acids by an L-histidine-derived sulfonamide-induced enantioselective esterification reaction

AU - Ishihara, Kazuaki

AU - Kosugi, Yuji

AU - Umemura, Shuhei

AU - Sakakura, Akira

PY - 2008

Y1 - 2008

N2 - (Chemical Equation Presented) The direct and catalytic kinetic resolution of racemic carboxylic acids bearing a Brønsted base such as O-protected α-hydroxy carboxylic acids and N-protected α-amino acids has been accomplished through an L-histidine-derived sulfonamide-induced enantioselective esterification reaction with tert-butyl alcohol for the first time. Highly asymmetric induction [S(kfast/kslow) = up to 56] has been achieved under the equilibrium between a chiral catalyst and two diastereomeric acylammonium salts through an intramolecular hydrogen-bonding interaction.

AB - (Chemical Equation Presented) The direct and catalytic kinetic resolution of racemic carboxylic acids bearing a Brønsted base such as O-protected α-hydroxy carboxylic acids and N-protected α-amino acids has been accomplished through an L-histidine-derived sulfonamide-induced enantioselective esterification reaction with tert-butyl alcohol for the first time. Highly asymmetric induction [S(kfast/kslow) = up to 56] has been achieved under the equilibrium between a chiral catalyst and two diastereomeric acylammonium salts through an intramolecular hydrogen-bonding interaction.

UR - http://www.scopus.com/inward/record.url?scp=55249119876&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=55249119876&partnerID=8YFLogxK

U2 - 10.1021/ol801007m

DO - 10.1021/ol801007m

M3 - Article

VL - 10

SP - 3191

EP - 3194

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 15

ER -