Asymmetric induction in the Darzens reaction by means of chiral phase-transfer in a two-phase system. The effect of binding the catalyst to a solid polymeric support
- 1 January 1978
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 1,p. 8-11
- https://doi.org/10.1039/p19780000008
Abstract
Reaction of carbonyl compounds with chloromethyl p-tolyl sulphone or with chloro(phenyl)acetonitrile in a two-phase system, in the presence of chiral ammonium salts, affords the corresponding oxirans with 0–2.5% optical yields. The presence of a hydroxy-group β to the ‘onium’ function is essential to achieve asymmetric induction. Asymmetric induction is increased by binding of the catalyst to a polymeric matrix to give optical yields up to 23%.Keywords
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