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Total synthesis of UCS1025A.
The enantioselective total synthesis of the telomerase inhibitor UCS1025A has been accomplished. The key transformation involves a remarkable boron Reformatsky coupling of iodolactone 13 and aldehydeExpand
Enantioselective Brønsted base catalysis with chiral cyclopropenimines.
Cyclopropenimines are shown to be a highly effective new class of enantioselective Brønsted base catalysts and the basicity of a 2,3-bis(dialkylamino)cyclopropanimine is measured for the first time and shows to be approximately equivalent to the P(1)-tBu phosphazene base. Expand
Cyclopropenimine-catalyzed enantioselective Mannich reactions of tert-butyl glycinates with N-Boc-imines.
Cyclopropenimine 1 is shown to catalyze Mannich reactions between glycine imines and N-Boc-aldimines with high levels of enantio- and diastereocontrol with substantially greater than that of a widely used thiourea cinchona alkaloid-derived catalyst. Expand
Aminocyclopropenium Ions: Synthesis, Properties, and Applications
This review covers the preparation, physical properties, and applications of cyclopropenium ions bearing one, two, or three amino substituents. It provides a description of the most reliable methodsExpand
Tropylium ion mediated α-cyanation of amines.
Even in the presence of KCN, tropylium ion is capable of oxidizing various amine substrates, and the resulting iminium ions undergo salt metathesis with cyanide ion to produce aminonitriles. Expand
Multicatalysis: Advancing Synthetic Efficiency and Inspiring Discovery
Heavy reliance on iterative synthetic strategies represents one of the most serious drawbacks of modern organic synthesis. There has been increasing interest of late in the development of processesExpand
Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication.
This chemistry employs a trisaminocyclopropium ion catalyst, which is electrochemically oxidized to form a cyclopropenium radical dication intermediate, which undergoes photoexcitation with visible light to produce an excited state species with oxidizing power sufficient to oxidize benzene and halogenated benzenes via single electron transfer (SET). Expand
Multicatalytic synthesis of alpha-pyrrolidinyl ketones via a tandem palladium(II)/indium(III)-catalyzed aminochlorocarbonylation/Friedel-Crafts acylation reaction.
  • T. Cernak, T. Lambert
  • Chemistry, Medicine
  • Journal of the American Chemical Society
  • 11 February 2009
An oxidative carbonylation reaction that generates acid chloride functionality has been developed and has been merged with a catalytic Friedel-Crafts acylation to produce a highly efficient tandem multicatalytic synthesis of pyrrolidinyl ketones. Expand
Asymmetric Induction via a Helically Chiral Anion: Enantioselective Pentacarboxycyclopentadiene Brønsted Acid-Catalyzed Inverse-Electron-Demand Diels-Alder Cycloaddition of Oxocarbenium Ions.
Computational and X-ray crystallographic analyses support the unique hypothesis that an anion with point-chirality-induced helical chirality dictates the absolute sense of stereochemistry in this reaction. Expand