63103-80-0Relevant academic research and scientific papers
Synthesis and chemistry of 10,11-dihydro-5-phenyl-5H-dibenzo[b, f]phosphepine 5-oxide, the 5-propyl analogue and related phosphonium salts
Warren, Stuart,Wyatt, Paul
, p. 249 - 255 (2007/10/03)
The preparation of the title compounds is greatly improved by combining seven steps (three lithiations, three substitutions and an oxidation) into a one-pot procedure. The hydrolysis of the related phosphonium salts, the lithiation of the P-propyl phosphepine oxides and their reaction with electrophiles are described.
REVERSED STEREOCHEMICAL CONTROL IN THE REGIOSELECTIVE REDUCTION OF HINDERED DIPHENYLPHOSPHINOYL (Ph2PO-) KETONES AND ENONES
Elliott, Jason,Hall, David,Warren, Stuart
, p. 601 - 604 (2007/10/02)
Reduction of α'-diphenylphosphinoyl enones (6) and crowded α-diphenylphosphinoyl ketones (4) with sodium borohydride in the presence of cerium chloride gives the otherwise difficult to obtain erythro-alcohols (5) and (7).
HORNER-WITTIG REACTIONS USING DIBENZOPHOSPHOLE OXIDES: STEREOCHEMICALLY CONTROLLED REDUCTION OF KETONES
Elliott, Jason,Warren, Stuart
, p. 645 - 648 (2007/10/02)
Reduction of ketones having an α-dibenzophosphole-5-oxide group with NaBH4, L-Selectride, or Superhydride gives threo Horner-Wittig intermediates and hence E-alkenes, while NaBH4/CeCl3 gives erythro intermediates and hence Z-alkenes.
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.
