89625-14-9

Upstream product

• 80403-10-7 oxyde de benzoyloxy-3 propyldiphenylphosphine 
• 889-57-6 3-(diphenylphosphinoyl)-1-propanol 
• 603-35-0 triphenylphosphine 
• 2129-89-7 diphenyl(methyl)phosphine oxide 
• 51860-45-8 3-hydroxypropyltriphenylphosphonium bromide 

Downstream Products

• 3481-02-5 cyclopropyl phenyl ketone 
• 39755-03-8 4-hydroxy-1-phenyl-butan-1-one 
• 89625-17-2 threo-2-diphenylphosphinoyl-1-phenylbutane-1,4-diol 
• 89625-17-2 erythro-2-Diphenylphosphinoyl-1-phenylbutane-1,4-diol 
• 122552-38-9 4-diphenylphosphinoxy-1-phenylbutan-1-one 
• 122552-34-5 3-benzoyl-3-diphenylphosphinoylpropyl benzoate 
• 20047-19-2 (Z)-4-phenylbut-3-en-1-ol 
• 937-58-6 (3E)-4-phenyl-3-buten-1-ol 

Relevant academic research and scientific papers

Asymmetric synthesis of trans-disubstituted cyclopropanes using phosphine oxides and phosphine boranes

The stereocontrolled synthesis of trans-disubstituted cyclopropylketones has been achieved from β-alkyl, γ-benzoyl phosphine oxides via a three-step cascade reaction incorporating an acyl transfer, phosphinoyl transfer and cyclisation to form the cyclopropane. Using Evans' chiral oxazolidinone auxiliary and by masking the phosphine oxide moiety as a phosphine borane we have extended the method to the synthesis of enantiomerically-enriched trans-disubstituted cyclopropyl ketones.

ACYL TRANSFER REACTIONS WITH PHOSPHINE OXIDES: SYNTHESIS OF E-HOMOALLYLIC ALCOHOLS, CYCLOPROPYL KETONES, AND γ-HYDROXY KETONES

Esters of 3-hydroxypropylphosphine oxides rearrange in base by O to C acyl (RCO) transfer to give the hydroxy ketones (8). threo-Selective reduction of (8) leads to pure E-homoallylic alcohols whilst C to O acyl )Ph2PO) transfer leads to γ-hydroxy ketones with nucleophilic aqueous base or cyclopropyl ketones with BuOKt - HOBut.

SYNTHESIS OF E-HOMOALLYLIC ALCOHOLS, γ-HYDROXYKETONES, AND CYCLOPROPYL KETONES FROM 3-DIPHENYLPHOSPHINOYL (Ph2PO) PROPANOLS BY ACYL TRANSFER

Carboxyl transfer (O*C) on 3-Ph2PO propyl esters (9) gives an intermediate (10) from which the Ph2PO group may be removed by the Horner-Witting reaction or by Ph2PO transfer (C*O) to give the title compounds.

SYNTHESIS OF SINGLE ISOMERS (E OR Z) OF UNSATURATED ALCOHOLS BY THE HORNER-WITTIG REACTION

Single isomers (E or Z) of homoallylic and higher alcohols can be synthesised from ω-hydroxyalkyldiphenylphosphine oxides and aldehydes, or from alkyldiphenylphosphine oxides and lactones