Site-selective catalysis of phenyl thionoformate transfer as a tool for regioselective deoxygenation of polyols.

ABSTRACT: We report the application of peptide-embedded imidazoles as catalysts for the site-selective delivery of the phenyl thionoformate unit as a prelude to deoxygenation reactions of polyols. Methodology was developed that allows for the synthesis of thiocarbonyl derivatives based on a combination of additives that include N-alkylimidazoles and FeCl3 as co-catalysts. The use of this reagent combination leads to increased reaction rates and efficient yields relative to those of simple base-mediated reactions. In terms of controlling regioselectivity during the course of polyol modification, we found that histidine-containing peptides, in combination with FeCl3, could lead to modulation of the product distribution. Through screening of peptides and control of reaction conditions, products could b

SUBMITTER: Sanchez-Rosello M 

PROVIDER: S-EPMC4189089 | biostudies-literature | 2008 Mar

REPOSITORIES: biostudies-literature