78266-84-9Relevant academic research and scientific papers
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.
CIS-OLEFINS FROM THE HORNER-WITTIG REACTION; ORIGIN AND OPTIMISATION OF STEREOCHEMISTRY
Buss, Antony D.,Warren, Stuart
, p. 3931 - 3934 (2007/10/02)
Conditions are described to produce high yields of erythro Horner-Wittig intermediates: stereospecific elimination gives cis-alkenes.
TRANS ALKENES BY STEREOSELECTIVE REDUCTION OF α-Ph2PO KETONES: E-ISOSAFFROLE, E-ANETHOLE, AND FENICULIN
Buss, Antony D.,Mason, Ralph,Warren, Stuart
, p. 5293 - 5296 (2007/10/02)
Conditions are described for the stereoselective reduction of α-Ph2PO ketones and stereospecific elimination from the resulting threo Horner-Witting intermediates to give pure E-alkenes such as the title compounds.
Stereochemically Pure E- and Z-Alkenes by the Wittig-Horner Reaction
Buss, Antony D.,Warren, Stuart
, p. 100 - 101 (2007/10/02)
Pure Z-alkenes are obtained stereospecifically from erythro-alcohols (3) formed on addition of Ph2PO-stabilised anions to aldehydes; acylation of the same anions, reduction of the α-Ph2P(O) ketones (5) to the threo-alcohol (6), and elimination gives pure E-alkenes.
