Indium-mediated allylations of alpha-heterosubstituted cyclohexanones in aqueous media

With the increasing pressure on the chemical and pharmaceutical industries to reduce their hazardous waste stream has come the demand to develop environmentally benign technologies. This goal has been espoused by President Clinton's Green Chemistry Challenge sponsored by the Environmental Protection Agency. Additionally, the National Research Council has focused on reducing the detrimental effects of chemicals to improve the environment.;Effective and efficient carbon-carbon bond forming reactions are the epitome of organic synthesis. Unfortunately, the majority of such transformations are extremely moisture sensitive requiring anhydrous organic solvents and air-sensitive organometallic reagents in an inert atmosphere of Ar or N;Recently several research groups have shown that the element indium (In) efficiently promotes allylation reactions in water. The allyl group is widely disseminated in organic chemistry and is often used as a key building block in the synthesis of natural and unnatural products. Further investigation of this intriguing water-based chemistry is thus warranted with particular attention to stereoselectivity. Stereoselectivity is a key feature of pharmaceutical synthesis as exemplified by the Federal Drug Administration's mandate requiring companies to produce enantiomerically pure drugs.;We undertook a comparative study of the allylindium reagent and some of the more traditional allylmetal reagents in reaction with ;The implications of this research are expected to be significant because of the inherent advantages. It is anticipated that this novel technology will be adopted by chemical and pharmaceutical industries in the near future and thereby drastically reduce environmental pollution and operational costs as well as increase workplace safety.