13303-58-7

Upstream product

• 63103-73-1 3-Diphenylphosphinoyl-4-trimethylsilylbutan-2-ol 
• 6117-91-5 (E/Z)-2-buten-1-ol 
• 1079-66-9 chloro-diphenylphosphine 
• 63103-39-9 diphenyl[2-(trimethylsilyl)ethyl]phosphine oxide 
• 2129-89-7 diphenyl(methyl)phosphine oxide 

Downstream Products

• 136679-72-6 (1'R^*,5R^*)-5-(1'-diphenylphosphinoylethyl)-3-methyl-4,5-dihydroisoxazole 
• 136679-73-7 (1'R^*,5R^*)-5-(1'-diphenylphosphinoylethyl)-3-propyl-4,5-dihydroisoxazole 
• 136679-73-7 (1'R^*,5S^*)-5-(1'-diphenylphosphinoylethyl)-3-propyl-4,5-dihydroisoxazoles 
• 136679-74-8 (1'R^*,5R^*)-5-(1'-diphenylphosphinoylethyl)-3-hexyl-4,5-dihydroisoxazole 
• 136679-74-8 (1'R^*,5S^*)-5-(1'-diphenylphosphinoylethyl)-3-hexyl-4,5-dihydroisoxazole 
• 71843-34-0 3-diphenylphosphinoyl-1-methylthiobut-2-ene 
• 113108-17-1 (<1-(2)H>-1-methylallyl)diphenyl phosphine oxide 
• 113108-15-9 (E)-3-diphenylphosphinoyl-1-phenylthiobut-2-ene 
• 113108-09-1 (E)-3-diphenylphosphinoyl-1-phenylthiobut-1-ene 
• 136679-75-9 (1'R^*,5R^*)-5-(1'-diphenylphosphinoylethyl)-3-phenyl-4,5-dihydroisoxazole 
• 136679-75-9 (1'R^*,5S^*)-5-(1'-diphenylphosphinoylethyl)-3-phenyl-4,5-dihydroisoxazole 
• 83877-77-4 1-cyclohexyl-2-methyl-(Z)-1,3-butadiene 
• 83877-79-6 1-cyclohexyl-2-methyl-(E)-1,3-butadiene 
• 69063-41-8 3-diphenylphosphinoyl-1-phenylthiobut-2-ene 

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.

A NEW ROUTE FOR THE CONVERSION OF CARVONE INTO EUDESMANE SESQUITERPENES

The β-hydroxy-α-phenylsulfenyl ketone 2, derived from S-(+)-carvone, was treated with 2 equivalents of the Wittig-Horner phosphine oxide derivative 6 followed by excess methyl iodide to give a ca. 2:3 mixture of the E and Z α-phenylsulfenyl ketones 3a and 3b.The mixture of sulfides was oxidized to the corresponding sulfoxides 3c,d with m-chloroperbenzoic acid.When this mixture refluxed in benzene, elimination of phenylsulfinic acid occured and the intermediate E diene derivative 4a underwent an intramolecular Diels-Alder reaction to give the trans-octalone 5a, the cis-octalone 5c, and another product believed to be the trans-octalone 5b in a 60:28:12 ratio.The Z diene derivative 4b was recovered under these reaction conditions.Wolff-Kishner reduction of the octalone mixture gave (-)-α-selinene (10) as the major product along with the cis-octalin 11 and other unidentified minor products.When the Z diene derivative 4b was heated in toluene at 150 deg C for 48 h, a mixture of octalones having the same composition as that produced above was obtained.Likewise, when the 2:3 mixture of sulfoxides 3c and 3d was heated in toluene at 150 deg C, the same mixture of octalones was produced.Apparently, at the higher temperature, the Z diene derivative 4b isomerized to the E isomer 4a which ultimately underwent the intramolecular Diels-Alder reaction.