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Issue 12, 1988
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Asymmetric synthesis of phenyl alkyl sulphoxides via the non-destructive mediation of the chiral iron acyl [(η5-C5H5)Fe(CO)(PPh3)COCH2Me]

Abstract

The chiral sulphoxide (RSS)-[(η5-C5H5)Fe(CO)(PPh3)COCHMeSOPh] can be efficiently and stereoselectively prepared from (R)-[(η5-C5H5)Fe(CO)(PPh3)COCH2Me]via the asymmetric oxidation of the corresponding sulphide: treatment of (RSS)-[(η5-C5H5)Fe(CO)(PPh3)COCHMeSOPh] with lithium dialkylcuprates afforded phenyl alkyl sulphoxides and regenerated (R)-[(η5-C5H5)Fe(CO)(PPh3)COCH2Me], while oxidative decomplexation led to (SS)-PhCH2NHCOCHMeSOPh; all the products were essentially enantiomerically pure.

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Article information


J. Chem. Soc., Chem. Commun., 1988, 780-781
Article type
Paper

Asymmetric synthesis of phenyl alkyl sulphoxides via the non-destructive mediation of the chiral iron acyl [(η5-C5H5)Fe(CO)(PPh3)COCH2Me]

S. G. Davies and G. L. Gravatt, J. Chem. Soc., Chem. Commun., 1988, 780
DOI: 10.1039/C39880000780

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