898528-32-0

Upstream product

• 1679-47-6 3-methyltetrahydro-2-furanone 
• 108-90-7 chlorobenzene 
• 423765-60-0 (-)-3-methyl-3-phenyl-dihydro-furan-2-one 

Downstream Products

• 898528-37-5 3-methyl-3-phenyl-pent-4-en-1-ol 
• 898528-44-4 allyl-(3-methyl-3-phenyl-pent-4-enyl)-amine 
• 898528-54-6 4-methyl-4-phenyl-2,3,4,7-tetrahydro-azepine-1-carboxylic acid benzyl ester 
• 898528-48-8 allyl-(3-methyl-3-phenyl-pent-4-enyl)-carbamic acid benzyl ester 
• 440369-05-1 (1S,2S)-1-cyclohexyl-2-methyl-2-phenylbutane-1,4-diol 

Relevant academic research and scientific papers

Regio- and stereoselective SN2′ reaction of an allylic picolinate in the synthesis of LY426965

Allylic substitution of secondary γ,γ-disubstituted allylic picolinates with ArMgBr-based copper reagents was applied to the synthesis of LY426965. Reduction of (R)-6-(PMB-oxy)-3-hexyn-2-ol of 93% ee (PMB = p-MeOC6H4CH2) using Red-Al gave (R,Z)-4-iodo-5-(PMB-oxy)hex-3-en-2-ol, which was later converted to the Me-substituted allylic picolinate by Pd-catalyzed coupling with MeZnI followed by esterification with picolinic acid. Allylic substitution with PhMgBr/Cu(acac)2 proceeded with high anti SN2′ selectivity (99%). Ozonolysis, addition of c-Hex-MgBr to the resulting aldehyde, and reductive amination with the piperazine derivative afforded LY426965.

Synthesis of 4,4′-disubstituted azepines via ring-closing metathesis reaction and asymmetric arylation of lactones

The syntheses of the title compounds were accomplished via an original sequence of reactions including the ring-closing metathesis of ω-dienes by using the second-generation Grubbs' catalyst. The chiral diene precursors are available in racemic or optical