Diastereofacial Control in the Reaction of (R)-α-(p-Tolylsulfinyl)acetophenones with Several Organometallics
- 5 September 1988
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 17 (9) , 1541-1544
- https://doi.org/10.1246/cl.1988.1541
Abstract
The diastereofacial controlled addition of organometallics to optically active β-ketosulfoxide was achieved to furnish both diastereomers of β-hydroxy sulfoxide depending on the selection of organometallic reagents. Trichloromethyltitanium added to (R)-α-(p-tolylsulfinyl)acetophenones to give (RsRc)-β-hydroxy sulfoxides, while (RsSc)-β-hydroxy sulfoxides were obtained by utilizing trimethylaluminum. The utility of the present reaction was demonstrated in the synthesis of both enantiomers of sydowic acid.Keywords
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