89091-84-9Relevant academic research and scientific papers
Diphenylphosphinoyl-mediated synthesis of ketones
Fox, David J.,Pedersen, Daniel Sejer,Warren, Stuart
, p. 3102 - 3107 (2008/02/14)
α-Diphenylphosphinoyl ketones are selectively and sequentially alkylated at the α-position. Double lithiation and selective alkylation occurs at the less stabilised γ-position. Dephosphinoylation of the alkylation products gives ketones. Mono-alkylation is selective, highly crystalline intermediates are formed and a one-pot strategy is possible. The method is ideally suited for the preparation of acid-sensitive ketones. The Royal Society of Chemistry 2006.
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.
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.
