Redox Selectivity through Hydrophobic Effects in Water

Columbia Univ New York Morningside, New York NY

Investigators

Abstract

DESCRIPTION: (provided by applicant) Directed, selective organic chemical reactions in water will lead to more efficient synthesis of medicinal compounds. Such reactions will shorten synthetic routes; lower the cost, hazards, and environmental impact associated with organic solvents at every stage of their use; and make possible transformations unachievable by current synthetic methodology. The ultimate goal of the proposed research is to further develop synthetic organic methodology in aqueous solution. Specifically, control of chemo-, regio-, and stereoselectivity by hydrophobic interactions in aqueous solution will be investigated in two systems: reduction with substituted cyanoborohydrides, and oxidation with dioxiranes derived from hydrophobic ketones. These reagents and the model substrates will be synthesized by established methods; product mixtures will be analyzed by HPLC.