Kevin M. Church

Catalytic stereocontrol of a radical cyclization

Abstract The stereochemistry of the free-radical chain mediated methylenecyclopentane annulation of olefins with 1 can be influenced significantly by the choice of catalyst radical. This suggests a new approach to the general problem of stereocontrol in radical reactions.

Methylenecyclopropanecarboxylates and -dicarboxylates, efficient reagents for the [3 + 2] methylenecyclopentane annulation of unactivated and electron-rich alkenes

Abstract The readily available methylenecyclopropanes 1 and 2 efficiently annulate unactivated and electron rich alkenes via a thiyl-radical catalyzed chain cyclization.

Efficient Pyrimidine N‐1‐Alkylation via Activation of Electron Rich Olefins with Oxoammonium Salts: Synthesis of Methoxy TEMPO Substituted Pyrimidine Nucleoside Analogs

Our work outlines the use of oxoammonium salts in a formal 1,2 addition process to olefins giving nucleoside analogs as products. Specifically, oxoammonium salts can be added to a solution of olefin and silylated heterocycle to give Methoxy TEMPO substituted nucleoside analogs after hydrolytic workup and chromatographic purification.

AMINO-THIOCYANATION OF ELECTRON RICH OLEFINS AS AN EFFICIENT PURINE AND PYRIMIDINE N-ALKYLATION PROCESS

ABSTRACT This work describes a relatively simple process to form thiocyanate substituted nucleoside mimics. ClSCN is slowly added to a solution of silylated heterocycle and suitable electron rich alkene. N-alkylated heterocycles are isolated in good yields after hydrolytic workup and flash chromatography.

Adenosine Nucleoside Analog Synthesis via Electrophilic Activation of Electron Rich Alkenes

Abstract Aminomercuration and aminoselenation of electron rich alkenes provides a useful route to adenosine nucleoside analogs.

Synthesis and DNA binding properties of tryptophan linked monocationic netropsin analogues

Abstract One tryptophan (Trp-Net) and two tryptophan (Trp-Trp-Net) residues have been linked to the amino terminus of a minor groove binding Netropsin analogue. DNA metling measurements indicate that Trp-Trp-Net binds significantly stronger than Trp-Net to double helical DNA. Both compounds induce helix extension as measured by changes in DNA viscosity indicating the possibility of intercalation of the tryptophan indole ring.