Affiliation:
1. Institute of Organic Chemistry (IOC), Karlsruhe Institute of Technology (KIT)
2. Institute of Biological and Chemical Systems - Functional Molecular Systems (IBCS-FMS), Karlsruhe Institute of Technology (KIT)
Abstract
AbstractBicyclopentanes (BCPs) are non-classical bioisosteres that have gained a lot of interest in drug discovery as non-conjugated rigid hydrocarbons. There has been substantial progress in the synthesis of carbon- and nitrogen-substituted derivatives using [1.1.1]propellane as a precursor, while sulfur-substituted BCPs are rather underdeveloped. This work investigates a new method for the synthesis of BCP-sulfoxides. Herein, a previously reported bench-stable sodium BCP-sulfinate precursor is converted, using a range of aryl and alkyl magnesium bromides, into unsymmetrical BCP-sulfoxides via a convenient one-pot procedure. Furthermore, the conversion of the obtained sulfoxides into sulfoximines is explored.
Funder
Deutsche Forschungsgemeinschaft