Asymmetric synthesis of sulfinyl-substituted arene chromium tricarbonyl complexes

Journal article

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.

Authors: Davies, S; Loveridge, T; Fatima, M; Teixeira, C; Clough, J

• Publication status: Published
• Journal: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
• Issue: 23
• Pages: 3405-3412
• Publication date: 1999-01-01
• DOI: 10.1039/a907590i
• EISSN: 1364-5463
• ISSN: 0300-922X
• Language: English