88533-67-9

Upstream product

• 63103-76-4 diphenyl 2-methylpropyl phosphine oxide 
• 100-52-7 benzaldehyde 
• 603-35-0 triphenylphosphine 
• 22884-29-3 isobutyltriphenylphosphonium bromide 
• 89091-86-1 2-diphenylphosphinoyl-3-methyl-1-phenylbutan-1-one 
• 93-89-0 benzoic acid ethyl ester 

Downstream Products

• 15325-61-8 (E)-(3-methylbut-1-en-1-yl)benzene 
• 15325-56-1 (Z)-3-methyl-1-phenylbut-1-ene 

Relevant academic research and scientific papers

The stereoselective Horner-Wittig reaction with phoshine oxides: Synthesis of hindered Z alkenes via Luche reduction

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.

REVERSED STEREOCHEMICAL CONTROL IN THE REGIOSELECTIVE REDUCTION OF HINDERED DIPHENYLPHOSPHINOYL (Ph2PO-) KETONES AND ENONES

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).

The Stereocontrolled Horner-Wittig Reaction: Synthesis of Disubstituted Alkenes

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

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

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.