Kinetically Controlled α-Selective O-Glycosylation of Phenol Derivatives Using 2-Nitroglycals by a Bifunctional Chiral Thiourea Catalyst

Keisuke Yoshida, Yohei Kanoko, Kenichi Takao

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

The highly α-selective organocatalytic glycosylation of phenol derivatives using 2-nitroglycals has been developed. The stereoselectivity of this reaction was kinetically controlled by a bifunctional thiourea catalyst, the chirality of which was crucial for obtaining the high α-selectivity. A variety of phenol derivatives were added to 2-nitrogalactal with excellent stereoselectivity. The reaction of 2-nitroglucal also achieved highly stereoselective glycosylation. The reaction was applied to the synthesis of glycopeptides.

Original languageEnglish
Pages (from-to)1230-1236
Number of pages7
JournalAsian Journal of Organic Chemistry
Volume5
Issue number10
DOIs
Publication statusPublished - 2016 Oct 1

Fingerprint

Glycosylation
Stereoselectivity
Thiourea
Phenol
Derivatives
Catalysts
Glycopeptides
Chirality

Keywords

  • carbohydrates
  • glycosylation
  • Michael addition
  • organocatalysis

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Kinetically Controlled α-Selective O-Glycosylation of Phenol Derivatives Using 2-Nitroglycals by a Bifunctional Chiral Thiourea Catalyst. / Yoshida, Keisuke; Kanoko, Yohei; Takao, Kenichi.

In: Asian Journal of Organic Chemistry, Vol. 5, No. 10, 01.10.2016, p. 1230-1236.

Research output: Contribution to journalArticle

@article{48c84648d57444939c158ad3d83ab941,
title = "Kinetically Controlled α-Selective O-Glycosylation of Phenol Derivatives Using 2-Nitroglycals by a Bifunctional Chiral Thiourea Catalyst",
abstract = "The highly α-selective organocatalytic glycosylation of phenol derivatives using 2-nitroglycals has been developed. The stereoselectivity of this reaction was kinetically controlled by a bifunctional thiourea catalyst, the chirality of which was crucial for obtaining the high α-selectivity. A variety of phenol derivatives were added to 2-nitrogalactal with excellent stereoselectivity. The reaction of 2-nitroglucal also achieved highly stereoselective glycosylation. The reaction was applied to the synthesis of glycopeptides.",
keywords = "carbohydrates, glycosylation, Michael addition, organocatalysis",
author = "Keisuke Yoshida and Yohei Kanoko and Kenichi Takao",
year = "2016",
month = "10",
day = "1",
doi = "10.1002/ajoc.201600307",
language = "English",
volume = "5",
pages = "1230--1236",
journal = "Asian Journal of Organic Chemistry",
issn = "2193-5807",
publisher = "Wiley - VCH Verlag GmbH & CO. KGaA",
number = "10",

}

TY - JOUR

T1 - Kinetically Controlled α-Selective O-Glycosylation of Phenol Derivatives Using 2-Nitroglycals by a Bifunctional Chiral Thiourea Catalyst

AU - Yoshida, Keisuke

AU - Kanoko, Yohei

AU - Takao, Kenichi

PY - 2016/10/1

Y1 - 2016/10/1

N2 - The highly α-selective organocatalytic glycosylation of phenol derivatives using 2-nitroglycals has been developed. The stereoselectivity of this reaction was kinetically controlled by a bifunctional thiourea catalyst, the chirality of which was crucial for obtaining the high α-selectivity. A variety of phenol derivatives were added to 2-nitrogalactal with excellent stereoselectivity. The reaction of 2-nitroglucal also achieved highly stereoselective glycosylation. The reaction was applied to the synthesis of glycopeptides.

AB - The highly α-selective organocatalytic glycosylation of phenol derivatives using 2-nitroglycals has been developed. The stereoselectivity of this reaction was kinetically controlled by a bifunctional thiourea catalyst, the chirality of which was crucial for obtaining the high α-selectivity. A variety of phenol derivatives were added to 2-nitrogalactal with excellent stereoselectivity. The reaction of 2-nitroglucal also achieved highly stereoselective glycosylation. The reaction was applied to the synthesis of glycopeptides.

KW - carbohydrates

KW - glycosylation

KW - Michael addition

KW - organocatalysis

UR - http://www.scopus.com/inward/record.url?scp=84991387493&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84991387493&partnerID=8YFLogxK

U2 - 10.1002/ajoc.201600307

DO - 10.1002/ajoc.201600307

M3 - Article

AN - SCOPUS:84991387493

VL - 5

SP - 1230

EP - 1236

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

SN - 2193-5807

IS - 10

ER -