Diastereoselectivity in Reactions of Lithiated 2-Phenylthiomethylthiotetrahydropyrans

Kaija Sipilä Laboratory of Organic Chemistry, Department of Chemistry, University of Helsinki, PO Box 55, University of Helsinki, FIN-00014, Finland

Tapio Hase Laboratory of Organic Chemistry, Department of Chemistry, University of Helsinki, PO Box 55, University of Helsinki, FIN-00014, Finland

Jorma Koskimies Laboratory of Organic Chemistry, Department of Chemistry, University of Helsinki, PO Box 55, University of Helsinki, FIN-00014, Finland

Jorma Matikainen Laboratory of Organic Chemistry, Department of Chemistry, University of Helsinki, PO Box 55, University of Helsinki, FIN-00014, Finland

Jarno Kansikas Laboratory of Inorganic Chemistry, Department of Chemistry, University of Helsinki, PO Box 55, University of Helsinki, FIN-00014, Finland

Abstract

Diastereoselectivities of up to 95:5 in alkylations of lithiated O,S,S-acetals are rationalized by the locked conformation of the five-membered ring caused by lithium-to-oxygen coordination. The relative configurations of the two diastereomers obtained in benzylation of lithiated 2-(phenylthiomethylthio)tetrahydropyran were confirmed by comparison with reference compounds of known stereochemistry obtained by benzylic reduction of crystalline hydroxyalkylated derivatives.

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Diastereoselectivity in Reactions of Lithiated 2-Phenylthiomethylthiotetrahydropyrans

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Diastereoselectivity in Reactions of Lithiated 2-Phenylthiomethylthiotetrahydropyrans

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