103785-93-9Relevant academic research and scientific papers
The stereoselective Horner-Wittig reaction with phoshine oxides: Synthesis of hindered Z alkenes via Luche reduction
Hutton,Jolliff,Mitchell,Warren
, p. 7905 - 7908 (2007/10/02)
The natural anti selectivity of the Horner-Wittig reaction with phospine oxides is reduced when there is a branched chain next to the new C=C double bond. A better approach is Luche reduction of the corresponding ketones which gives high anti selectivity when the branched chain is placed on the side chain next to the phosphine oxide.
The Stereocontrolled Horner-Wittig Reaction: Synthesis of Disubstituted Alkenes
Buss, Antony D.,Warren, Stuart
, p. 2307 - 2326 (2007/10/02)
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.
