Unexpected reactions of Grignard reagents with selected β-carboalkoxy substituted sulfinate esters

摘要: A series of six-membered rings bearing cis oriented vicinal carboxylate and sulfinate esters were treated with Grignard reagents the intention transforming them to β-carboalkoxy substituted sulfoxides. The expected outcome did not transpire instead substrates demonstrated capacity accept 3 equiv. organometallic agent in an uncontrollable manner. As such, possessing eclipsing accepted two organic ligands at functionality one sulfinyl group. When isomer mixtures sterically encumbered reacted, a single sulfoxide stereochemistry resulted. mechanism involving intermediacy sulfurane is proposed account for experimental observations.