The stereocontrolled Horner-Wittig reaction: synthesis of disubstituted alkenes
- 1 January 1985
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 2307-2325
- https://doi.org/10.1039/p19850002307
Abstract
Addition of the lithium derivatives of phosphine oxides Ph2P(O)CH2R1 to aldehydes gives erythro adducts (11) with good stereoselectivity. Reduction of α-diphenylphosphinoyl ketones (12) gives threo adducts (11) with even better stereoselectivity. Purification by flash chromatography and/or crystallisation followed by elimination of Ph2PO2) gives pure Z- or E-alkenes with high material conversion. Explanations are offered for the stereoselectivities, conditions defined for full stereochemical control, and guidelines suggested for approaches to a given alkene.Keywords
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