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A Platform for the Discovery of New Macrolide Antibiotics
(2016-04-25)
The macrolide class of antibiotics has been widely used to treat bacterial infections for over 65 years. To date, all practical routes to clinically used macrolide antibiotics have relied on the chemical modification of ...
Reactivity and Selectivity in Aryl C–H Functionalization by Electrophilic Radicals
(2016-05-04)
Two main challenges hinder the development of new, broadly useful C–H functionalization reactions: (1) most C–H bonds constitute part of the relatively inert backbone of an organic molecule, so it is difficult to elicit ...
Investigations of the Biosynthesis and Structure of Colibactin, a Cytotoxin Made by Human-Associated Escherichia Coli
(2016-01-13)
Humans exist in symbiosis with trillions of bacteria that are collectively referred to as the human microbiota. While commensal microbes are essential for health, some resident microbes can promote disease. Certain strains ...
Engaging Chiral Cationic Intermediates by Anion-Binding in Asymmetric Catalysis
(2016-01-13)
Anion-binding catalysis by dual hydrogen-bond donors such as ureas and squaramides has been demonstrated as a powerful strategy for the development of highly enantioselective transformations involving prochiral cationic ...
A Mechanistic Approach Towards Highly Efficient Anion-Binding Catalysts
(2016-09-14)
Over the past decade, organocatalysis has emerged as a thriving area of research in the field of small-molecule asymmetric catalysis. In this context, the development of highly efficient catalysts—i.e. TON ≥ 1000, TOF ≥ ...
Activation of Weak Nucleophiles in Anion-Binding Catalysis
(2016-09-14)
Anion-binding catalysis has emerged as a powerful principle for the development of highly enantioselective transformations. This strategy relies on the ability of dual hydrogen-bond donors to promote anion abstraction from ...
Palladium-Catalyzed Arene Functionalization via Single-Electron Reduction of Selectfluor
(2016-08-26)
Palladium-catalysis is commonly used in the functionalization of aromatic rings, ranging from prefunctionalized substrates such as aryl metals or aryl (pseudo)halides to the direct functionalization of aromatic C–H bonds. ...
Late-Stage Fluorination With 19F− and 18F− via Concerted Nucleophilic Aromatic Substitution
(2016-09-09)
The formation of C–F bonds has long been considered a challenging transformation and C–F bonds commonly had to be formed early on in a synthetic sequence towards complex organofluorides. Late-stage fluorination reactions ...
Cooperative Asymmetric Catalysis with Squaramide H-Bond Donors and Lewis Acids
(2016-07-28)
A new mode of cooperative catalysis with chiral squaramide hydrogen-bond donors and trialkylsilyl trifluoromethanesulfonates (triflates) for asymmetric nucleophilic additions to oxocarbenium ions was explored. Evidence is ...
I. Chiral Squaramide Catalysts for Lewis Acid Activation in Asymmetric Catalysis II. Catalytic, Stereoselective Difluorination Reactions
(2016-12-13)
In Chapter 1, we report the observation that chiral squaramide hydrogen-bond (H-bond) donor catalysts act cooperatively with trialkylsilyl trifluoromethanesulfonates (silyl triflates) to promote enantioselective (4+3) ...