Catalytic approaches to chemo-and site-selective transformation of carbohydrates

K Yamatsugu, M Kanai - Chemical Reviews, 2023 - ACS Publications
Carbohydrates are a fundamental unit playing pivotal roles in all the biological processes. It
is thus essential to develop methods for synthesizing, functionalizing, and manipulating …

Site-selective functionalization of hydroxyl groups in carbohydrate derivatives

V Dimakos, MS Taylor - Chemical reviews, 2018 - ACS Publications
Methods for site-selective transformations of hydroxyl groups in carbohydrate derivatives are
reviewed. The construction of oligosaccharides of defined connectivity hinges on such …

Catalytic glycosylations in oligosaccharide synthesis

MM Nielsen, CM Pedersen - Chemical Reviews, 2018 - ACS Publications
Catalytic glycosylation has been a central reaction in carbohydrate chemistry since its
introduction by Fischer 125 years ago, but it is only in the past three to four decades that …

Nonenzymatic Stereoselective S-Glycosylation of Polypeptides and Proteins

LQ Wan, X Zhang, Y Zou, R Shi, JG Cao… - Journal of the …, 2021 - ACS Publications
Here we report a nonenzymatic glycosylation reaction that builds axial S-glycosidic bonds
under biorelevant conditions. This strategy is enabled by the design and use of allyl glycosyl …

Oxalic Diamides and tert-Butoxide: Two Types of Ligands Enabling Practical Access to Alkyl Aryl Ethers via Cu-Catalyzed Coupling Reaction

Z Chen, Y Jiang, L Zhang, Y Guo… - Journal of the American …, 2019 - ACS Publications
A robust and practical protocol for preparing alkyl aryl ethers has been developed, which
relies on using two types of ligands to promote Cu-catalyzed alkoxylation of (hetero) aryl …

Synthesis of a C2-Symmetric Chiral Borinic Acid and Its Application in Catalytic Desymmetrization of 2,2-Disubstituted-1,3-Propanediols

J Song, WH Zheng - Journal of the American Chemical Society, 2023 - ACS Publications
Notwithstanding the common use of boronic acids in catalysis, the design and synthesis of
efficient chiral boronic acids remains a formidable challenge. Herein we disclose a rational …

Asymmetric Pd/Organoboron‐Catalyzed Site‐Selective Carbohydrate Functionalization with Alkoxyallenes Involving Noncovalent Stereocontrol

H Guo, JL Kirchhoff, C Strohmann, B Grabe… - Angewandte …, 2024 - Wiley Online Library
Herein, we demonstrate the robustness of a synergistic chiral Pd/organoboron system in
tackling a challenging suite of site‐, regio‐, enantio‐and diastereoselectivity issues across a …

Generation of Glycosyl Radicals from Glycosyl Sulfoxides and Its Use in the Synthesis of C‐linked Glycoconjugates

W Shang, SN Su, R Shi, ZD Mou, GQ Yu… - Angewandte Chemie …, 2021 - Wiley Online Library
We here report glycosyl sulfoxides appended with an aryl iodide moiety as readily available,
air and moisture stable precursors to glycosyl radicals. These glycosyl sulfoxides could be …

Ni-Catalyzed Suzuki–Miyaura Cross-Coupling of α-Oxo-vinylsulfones To Prepare C-Aryl Glycals and Acyclic Vinyl Ethers

L Gong, HB Sun, LF Deng, X Zhang, J Liu… - Journal of the …, 2019 - ACS Publications
We demonstrate that readily available and bench-stable α-oxo-vinylsulfones are competent
electrophiles in Ni-catalyzed Suzuki–Miyaura cross-coupling reactions. The C–sulfone bond …

A synergistic Rh (I)/organoboron-catalysed site-selective carbohydrate functionalization that involves multiple stereocontrol

VUB Rao, C Wang, DP Demarque, C Grassin, F Otte… - Nature Chemistry, 2023 - nature.com
Site-selective functionalization is a core synthetic strategy that has broad implications in
organic synthesis. Particularly, exploiting chiral catalysis to control site selectivity in complex …