Studies of the mechanism and origins of enantioselectivity for the chiral phosphoric acid-catalyzed stereoselective spiroketalization reactions

YY Khomutnyk, AJ Argüelles… - Journal of the …, 2016 - ACS Publications
Mechanistic and computational studies were conducted to elucidate the mechanism and the
origins of enantiocontrol for asymmetric chiral phosphoric acid-catalyzed spiroketalization …

Catalytic Transfer Vinylation of Alcohols

S Opačak, S Tin - Advanced Synthesis & Catalysis, 2024 - Wiley Online Library
This review focuses on summarising the studies on transition metal catalysed transfer
vinylation of alcohols using vinyl ethers and vinyl acetate as vinylating agents. Mercury …

Quantitative DFT modeling of the enantiomeric excess for dioxirane-catalyzed epoxidations

ST Schneebeli, ML Hall, R Breslow… - Journal of the American …, 2009 - ACS Publications
Herein we report the first fully quantum mechanical study of enantioselectivity for a large
data set. We show that transition state modeling at the UB3LYP-DFT/6-31G* level of theory …

Advancements in the Synthesis of Polyoxygenated Oxepanes and Thiepanes for Applications to Natural Products

AR Pote, SM Weierbach, M Peczuh… - Organic Chemistry …, 2024 - pubs.rsc.org
Oxepanes are central motifs and tenants of many biologically important molecules, and their
synthetic construction often presents a challenge to chemists due to consequential entropic …

The price of flexibility–a case study on septanoses as pyranose mimetics

CP Sager, B Fiege, P Zihlmann, R Vannam… - Chemical …, 2018 - pubs.rsc.org
Seven-membered ring mimetics of mannose were studied as ligands for the mannose-
specific bacterial lectin FimH, which plays an essential role in the first step of urinary tract …

A unified strategy targeting the thiodiketopiperazine mycotoxins exserohilone, gliotoxin, the epicoccins, the epicorazines, rostratin A and aranotin

U Gross, M Nieger, S Bräse - Chemistry–A European Journal, 2010 - Wiley Online Library
A unified synthetic strategy directed towards mycotoxins belonging to the
thiodiketopiperazine family is reported. The building blocks for a number of natural products …

Stereoelectronic factors in the stereoselective epoxidation of glycals and 4-deoxypentenosides

L Alberch, G Cheng, SK Seo, X Li… - The Journal of …, 2011 - ACS Publications
Glycals and 4-deoxypentenosides (4-DPs), unsaturated pyranosides with similar structures
and reactivity profiles, can exhibit a high degree of stereoselectivity upon epoxidation with …

Synthesis of aryl, glycosyl, and azido septanosides through ring expansion of 1, 2-cyclopropanated sugars

NV Ganesh, N Jayaraman - The Journal of Organic Chemistry, 2009 - ACS Publications
A ring-expansion methodology for the preparation of aryl septanosides, arabinofuranosyl
and glucopyranosyl septanoside disaccharides, and azido septanosides is reported. A …

Synthesis and properties of septanose carbohydrates

J Saha, MW Peczuh - Advances in Carbohydrate Chemistry and …, 2011 - Elsevier
Seven-atom ring sugars, called septanoses, are increasingly the focus of scientific inquiries
because of their potential biological activities. This article details the synthesis …

1,5-α-d-Mannoseptanosides, Ring-Size Isomers That Are Impervious to α-Mannosidase-Catalyzed Hydrolysis

MA Boone, FE McDonald, J Lichter, S Lutz, R Cao… - Organic …, 2009 - ACS Publications
1, 5-d-Mannoseptanosyl di-and trisaccharide ring-size isomers of the corresponding
mannopyranosyl oligosaccharides have been prepared. Remarkably, these compounds …