259145-10-3Relevant academic research and scientific papers
Asymmetric synthesis of sulfinyl-substituted arene chromium tricarbonyl complexes
Davies, Stephen G.,Loveridge, Tracey,Teixeira, M. Fatima C. C.,Clough, John M.
, p. 3405 - 3412 (2007/10/03)
The synthesis of (SRSs[(phenylsulfinyl)benzene] chromium tricarbonyl 5 and (SRSs)-[(p-tolylsulfiny))benzene] chromium tricarbonyl 6 is achieved via a nucleophilic displacement reaction between the anion derived from (benzene) chromium tricarbonyl 9 and a suitable sulfinate ester. Replacing the sulfinate ester with a chiral sulfinyl-transfer reagent allows the isolation of the non-racemic sulfinyl-substituted complexes with good enantioselectivities (ee 80-89%) under optimised conditions. The use of Kagan's cyclic sulfite methodology for the synthesis of an enantiomerically pure tert-butylsulfinyl complex is unsuccessful, but results in the identification of a novel fragmentation - isomerisation process of the intermediate sulfinate. The Royal Society of Chemistry 1999.
