136869-33-5

Upstream product

• 873-67-6 benzonitrile oxide 
• 136679-94-2 (1R^*,3R^*,4R^*)-1-amino-4-diphenylphosphinoyl-1-phenylpentan-3-ol 
• 136679-75-9 (1'R^*,5R^*)-5-(1'-diphenylphosphinoylethyl)-3-phenyl-4,5-dihydroisoxazole 
• 165683-43-2 (E)-1-phenylpent-3-en-1-amine 

Relevant academic research and scientific papers

A New Method for Stereoselective Homoallylic Amine Synthesis

Nitrile oxide cycloadditions to readily available allylic diphenylphosphine oxides 2 proceeded regioselectively and stereoselectively to give 5-(1'-diphenylphosphinoylalkyl)isoxazolines 4 and 5.These heterocycles were reduced to δ-amino-β-hydroxyalkyldiphenylphosphine oxides 6 and 7 using a combination of sodium borohydride and nickel(II) chloride.Stereospecific elimination of diphenylphosphinic acid from the reduction products using sodium hydride in N,N-dimethylformamide gave homoallylic primary amines 8 and 9 of defined stereochemistry.

Stereocontrolled synthesis of homoallylic amines using phosphine oxides and isoxazolines

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.