Synthesis of Complex Allylic Esters via C−H Oxidation vs C−C Bond Formation

Palladium-catalyzed selective anti-Markovnikov oxidation of allylic esters.

Catalytic asymmetric carbon-carbon bond formation via allylic alkylations with organolithium compounds.

Carbon-carbon bond formation is the basis for the biogenesis of nature's essential molecules. Consequently, it lies at the heart of the chemical sciences. Chiral catalysts have been developed for asymmetric C-C bond formation to yield single enantiomers from several organometallic reagents. Remarkably, for extremely reactive organolithium compounds, which are among the most broadly used reagent...

An efficient and general route to reduced polypropionates via Zr-catalyzed asymmetric CC bond formation.

An efficient and general method for the synthesis of reduced polypropionates has been developed through the application of asymmetric carboalumination of alkenes catalyzed by dichlorobis(1-neomenthylindenyl)zirconium [(NMI)(2)ZrCl(2)]. In this investigation, attention has been focused on those reduced polypropionates that are alpha-monoheterofunctional and either omega-ethyl or omega-n-propyl. ...

Synthesis of functionalized allylic, propargylic and allenylic compounds Selective formation of CB, CC, CCF3 and CSi bonds

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C-C bond formation via C-H bond activation: synthesis of the core of teleocidin B4.

The core of teleocidin B4, a complex fragment of a natural product containing two quaternary stereocenters and a penta-substituted benzene ring, was synthesized in four C-C bond-forming steps starting from tert-butyl derivative 1. The first step involved alkenylation of the tert-butyl group with a vinyl boronic acid, followed by the successful annulation of the cyclohexane ring to the benzene n...