A variety of di- and trisubstituted thiophenes were synthesized by a one-pot palladium-catalyzed ortho-alkylation sequence terminated by either Heck or C-H coupling. Initial results toward the functionalization of indoles are also presented.
A new three-component, palladium-catalyzed domino reaction which gives access to meta-substituted arenes using aryl iodides and primary alkyl halides is reported. Various functional groups are tolerated on both the aryl iodide and alkyl halide. In addition, isotopic labeling studies provide insight into the mechanism of this Catellani-type reaction. [reaction: see text]
Several Pd-catalyzed cyclization methods were developed, including norbornenemediated Catellani-type reactions, a Pd-catalyzed coupling reaction of aryl iodides and allyl moieties, and a tandem C-N/C-C coupling of gem-dihalovinyl systems. These ring-forming methods were applied to the synthesis of highly functionalized carbocyclic and heterocyclic compounds. Intermolecular Pd-catalyzed methods for synthesis of highly substituted arene compounds were also developed.
The kinetic enzymatic resolution of cyclopropane acetates was systematically investigated utilizing 16 different hydrolases. Best results were obtained with hydrolyses in the presence of Candida antarctica B lipase.
A short, high-yielding synthesis of the marine oxylipins constanolactone A and B was reported. Starting from cinnamyl alcohol (3), the cylopropyl lactone moiety 2 was obtained in 28% yield (11 steps). The second coupling partner, vinyl iodide 1, was isolated in 7 steps and 32% yield. Chromium mediated addition yielded the natural products as a 2:1 mixture (74%).
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