Pd-catalyzed coupling reactions of anhydro-aldose tosylhydrazones with aryl bromides to produce substituted exo-glycals

Tímea Kaszás, Anton Ivanov, M. Tóth, Peter Ehlers, Peter Langer, L. Somsák

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Palladium-catalyzed cross-couplings of O-peracylated and O-permethylated 2,6-anhydro-aldose tosylhydrazones with aryl halides were studied under thermic conditions in the presence of LiO. tBu and phosphine ligands. The reactions gave the corresponding aryl substituted exo-glycals as mixtures of diastereomers in 11-75% yields. The transformations represent a new access to these types of glycomimetic compounds. The double bond of some aryl substituted exo-glycals was saturated to give good yields of benzylic C-glycosyl derivatives.

Original languageEnglish
JournalCarbohydrate Research
DOIs
Publication statusAccepted/In press - Jan 1 2018

Fingerprint

phosphine
Palladium
Bromides
Hot Temperature
Ligands
Derivatives

Keywords

  • Anhydro-aldose tosylhydrazones
  • Carbenes
  • Cross coupling
  • Pd-catalysis
  • Substituted exo-glycals

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

Cite this

Pd-catalyzed coupling reactions of anhydro-aldose tosylhydrazones with aryl bromides to produce substituted exo-glycals. / Kaszás, Tímea; Ivanov, Anton; Tóth, M.; Ehlers, Peter; Langer, Peter; Somsák, L.

In: Carbohydrate Research, 01.01.2018.

Research output: Contribution to journalArticle

@article{aaa06e09bbc54cbcbe08440913c48370,
title = "Pd-catalyzed coupling reactions of anhydro-aldose tosylhydrazones with aryl bromides to produce substituted exo-glycals",
abstract = "Palladium-catalyzed cross-couplings of O-peracylated and O-permethylated 2,6-anhydro-aldose tosylhydrazones with aryl halides were studied under thermic conditions in the presence of LiO. tBu and phosphine ligands. The reactions gave the corresponding aryl substituted exo-glycals as mixtures of diastereomers in 11-75{\%} yields. The transformations represent a new access to these types of glycomimetic compounds. The double bond of some aryl substituted exo-glycals was saturated to give good yields of benzylic C-glycosyl derivatives.",
keywords = "Anhydro-aldose tosylhydrazones, Carbenes, Cross coupling, Pd-catalysis, Substituted exo-glycals",
author = "T{\'i}mea Kasz{\'a}s and Anton Ivanov and M. T{\'o}th and Peter Ehlers and Peter Langer and L. Soms{\'a}k",
year = "2018",
month = "1",
day = "1",
doi = "10.1016/j.carres.2018.02.010",
language = "English",
journal = "Carbohydrate Research",
issn = "0008-6215",
publisher = "Elsevier BV",

}

TY - JOUR

T1 - Pd-catalyzed coupling reactions of anhydro-aldose tosylhydrazones with aryl bromides to produce substituted exo-glycals

AU - Kaszás, Tímea

AU - Ivanov, Anton

AU - Tóth, M.

AU - Ehlers, Peter

AU - Langer, Peter

AU - Somsák, L.

PY - 2018/1/1

Y1 - 2018/1/1

N2 - Palladium-catalyzed cross-couplings of O-peracylated and O-permethylated 2,6-anhydro-aldose tosylhydrazones with aryl halides were studied under thermic conditions in the presence of LiO. tBu and phosphine ligands. The reactions gave the corresponding aryl substituted exo-glycals as mixtures of diastereomers in 11-75% yields. The transformations represent a new access to these types of glycomimetic compounds. The double bond of some aryl substituted exo-glycals was saturated to give good yields of benzylic C-glycosyl derivatives.

AB - Palladium-catalyzed cross-couplings of O-peracylated and O-permethylated 2,6-anhydro-aldose tosylhydrazones with aryl halides were studied under thermic conditions in the presence of LiO. tBu and phosphine ligands. The reactions gave the corresponding aryl substituted exo-glycals as mixtures of diastereomers in 11-75% yields. The transformations represent a new access to these types of glycomimetic compounds. The double bond of some aryl substituted exo-glycals was saturated to give good yields of benzylic C-glycosyl derivatives.

KW - Anhydro-aldose tosylhydrazones

KW - Carbenes

KW - Cross coupling

KW - Pd-catalysis

KW - Substituted exo-glycals

UR - http://www.scopus.com/inward/record.url?scp=85042648368&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85042648368&partnerID=8YFLogxK

U2 - 10.1016/j.carres.2018.02.010

DO - 10.1016/j.carres.2018.02.010

M3 - Article

C2 - 29499901

AN - SCOPUS:85042648368

JO - Carbohydrate Research

JF - Carbohydrate Research

SN - 0008-6215

ER -