Phenylsulphonyloxiranes as functionalised acyl anion equivalents in organic synthesis
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 4,p. 897-908
- https://doi.org/10.1039/p19910000897
Abstract
Phenylsulphonyloxiranes can be lithiated with butyllithium α to the phenylsulphonyl group at low temperature. The anions formed are unstable, but sufficiently reactive to allow the isolation of adducts in good yield following treatment with a variety of electrophiles. Reaction of functionalised phenylsulphonyloxiranes with magnesium bromide–diethyl ether at room temperature allows the preparation of synthetically useful α-bromo ketones with complete regiocontrol.Keywords
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