Synthesis of E- and Z-vinyl ethers by the Horner–Wittig reaction
- 1 January 1979
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 3099-3106
- https://doi.org/10.1039/p19790003099
Abstract
Diphenyl(methoxymethyl)- and diphenyl-(1-methoxyethyl)-phosphine oxides form lithium derivatives which add to aldehydes and ketones. The adducts may be separated into crystalline diastereoisomers each giving a single geometrical isomer of a vinyl ether on treatment with base. Hydrolysis of the vinyl ethers provides a reliable aldehyde synthesis in which the lithium derivative (19) behaves as a formyl anion equivalent. The method has been used to convert an acyl indole into a vinyl ether in compounds related to the strychnos alkaloids.Keywords
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