Phosphine-Free Suzuki–Miyaura Cross-Coupling in Aqueous Media Enables Access to 2-C-Aryl-Glycosides

A general strategy for the synthesis of 2-aryl-glycals and their elaboration to 2-C-aryl-α-glycosides and 1,5-anhydro-2-C-aryl-2-deoxy alditols are described. The use of reliable, efficient phosphine-free Suzuki–Miyaura cross-coupling of 2-iodoglycals in aqueous media as a key step proceeds with com...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 14; no. 7; pp. 1728 - 1731
Main Authors Cobo, Isidro, Matheu, M. Isabel, Castillón, Sergio, Boutureira, Omar, Davis, Benjamin G
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.04.2012
Amer Chemical Soc
Subjects
Catalysis
Chemistry
Chemistry, Organic
Glycosides - chemical synthesis
Glycosides - chemistry
Molecular Structure
Phosphines
Physical Sciences
Science & Technology
Water
C-GLYCOSIDE SYNTHESIS
ORGANIC-SYNTHESIS
ARYL GLYCOSIDES
EFFICIENT SYNTHESIS
STEREOSELECTIVE-SYNTHESIS
GLYCOSYLTRANSFERASE INHIBITORS
ARYLBORONIC ACIDS
EXO-GLYCALS
CARBOHYDRATE-CHEMISTRY
PERACETYLATED GLYCALS
Online AccessGet full text

Cover

More Information
Summary:A general strategy for the synthesis of 2-aryl-glycals and their elaboration to 2-C-aryl-α-glycosides and 1,5-anhydro-2-C-aryl-2-deoxy alditols are described. The use of reliable, efficient phosphine-free Suzuki–Miyaura cross-coupling of 2-iodoglycals in aqueous media as a key step proceeds with complete regioselectivity at C-2 and enables access to 2-aryl-glycals with different configurations in excellent yields.
Bibliography:UKRI
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol3003139