136679-79-3Relevant academic research and scientific papers
The Synthesis of E Enol Ethers of Protected 4-Amino Aldehydes
Armstrong, Susan K.,Collington, Eric W.,Warren, Stuart
, p. 515 - 520 (2007/10/02)
The title compounds, a novel class of protected homoallylic amines, have been synthesised by a short and efficient route.Acrolein acetals were converted by a modified Michaelis-Arbuzov reaction into α-alkoxyallyl(diphenyl)phosphine oxides. 1,3-Dipolar cycloaddition to the alkene part of these molecules gave 5-diphenylphosphinoyl-4,5-dihydroisoxazoles, which were reductively cleaved to obtain δ-amino-β-hydroxy-α-alkoxyalkyl(diphenyl)phosphine oxides.After selective protection as the N-acyl derivatives, stereospecific Wittig-Horner diphenylphosphinic acid elimination gave the title compounds.
Stereocontrolled synthesis of homoallylic amines using phosphine oxides and isoxazolines
Armstrong, Susan K.,Warren, Stuart,Collington, Eric W.,Naylor, Alan
, p. 4171 - 4174 (2007/10/02)
Allylic diphenylphosphine oxides (7) undergo stereo selective 1,3-dipolar cycloadditions with nitrile oxides to give Δ2-isoxazolines (8). These may be reduced, also stereoselectively, to δ-amino-β-hydroxyalkyldiphenylphosphine oxides (9). Stereospecific Wittig-Horner type elimination of Ph2PO2-from amino alcohols (9) gives homoallylic amines (10) with controlled double bond geometry.
