101680-93-7Relevant academic research and scientific papers
Stereochemically controlled Synthesis of Unsaturated Alcohols by the Horner-Wittig Reaction
Ayrey, Peter M.,Bolton, Michael A.,Buss, Antony D.,Greeves, Nicholas,Levin, Daniel,et al.
, p. 3407 - 3418 (2007/10/02)
Single isomers (E or Z) of unsaturated alcohols with two to five carbon atoms between the double bond and the OH group may be made by the phosphine oxide version of the Horner-Wittig reaction.Hydroxyalkyldiphenylphosphine oxides react with aldehydes either directly or as silyl ethers to give a moderately Z-selective synthesis, while rearrangement of esters of the same alcohols by acyl transfer or acylation of alkyldiphenylphosphine oxides with lactones gives hydroxy ketones whose reduction and elimination leads to an E-selective synthesis.In most cases, separation of the diastereoisomers of the Horner-Wittig intermediates leads to the preparation of pure E- or Z-alkenols.
ACYL TRANSFER REACTIONS WITH PHOSPHINE OXIDES: SYNTHESIS OF E-HOMOALLYLIC ALCOHOLS, CYCLOPROPYL KETONES, AND γ-HYDROXY KETONES
Wallace, Paul,Warren, Stuart
, p. 2971 - 2978 (2007/10/02)
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
Wallace, Paul,Warren, Stuart
, p. 5713 - 5716 (2007/10/02)
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.
