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 …

Methods for 2-deoxyglycoside synthesis

CS Bennett, MC Galan - Chemical reviews, 2018 - ACS Publications
Deoxy-sugars often play a critical role in modulating the potency of many bioactive natural
products. Accordingly, there has been sustained interest in methods for their synthesis over …

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 …

Site-selective and stereoselective C–H alkylations of carbohydrates via combined diarylborinic acid and photoredox catalysis

V Dimakos, HY Su, GE Garrett… - Journal of the American …, 2019 - ACS Publications
Diphenylborinic acid serves as a cocatalyst for site-and stereoselective C–H alkylation
reactions of carbohydrates under photoredox conditions using quinuclidine as the hydrogen …

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 …

Borinic acid catalyzed stereo-and regioselective couplings of glycosyl methanesulfonates

KA D'Angelo, MS Taylor - Journal of the American Chemical …, 2016 - ACS Publications
In the presence of a diarylborinic acid catalyst, glycosyl methanesulfonates engage in regio-
and stereoselective couplings with partially protected pyranoside and furanoside acceptors …

Catalysis based on reversible covalent interactions of organoboron compounds

MS Taylor - Accounts of Chemical Research, 2015 - ACS Publications
Conspectus An Account of the development of organoboron-catalyzed methods for chemo-
or regioselective activation of pyruvic acids, diols, and carbohydrate derivatives is …

Synergistic organoboron/palladium catalysis for regioselective N-allylations of azoles with allylic alcohols

MT Zambri, TR Hou, MS Taylor - Organic Letters, 2022 - ACS Publications
A method for regioselective palladium-catalyzed allylic alkylation of ambident nitrogen
heterocycles, employing simple allylic alcohols as electrophile precursors, is described. An …

Site-divergent delivery of terminal propargyls to carbohydrates by synergistic catalysis

RZ Li, H Tang, L Wan, X Zhang, Z Fu, J Liu, S Yang… - Chem, 2017 - cell.com
Carbohydrate-containing molecules are ubiquitous in nature and essential to sustaining
lives. Selective modification of carbohydrates provides tremendous opportunities to …