454479-63-1

Upstream product

• 100-07-2 4-methoxy-benzoyl chloride 
• 585-32-0 2-phenyl-2-propylamine 

Downstream Products

• 1252815-37-4 2-iodo-4-methoxy-N-cumylbenzamide 
• 454479-66-4 (1S,3aR,4S,7aS)-4-methyl-3,6-dioxo-1-phenyl-octahydro-isoindole-2-carboxylic acid tert-butyl ester 
• 454479-65-3 (3S,3aS,7S,7aR)-7-methyl-3-phenylperhydro-isoindole-1,5-dione 
• 848476-32-4 (3R,3aR,7R,7aS)-hexahydro-7-(1-triisopropylsilyloxy)propyl-3-phenyl-2-(2-phenylpropan-2-yl)-6H-isoindole-1,5-dione 
• 848476-33-5 (1R,3aS,4R,4aR)-tert-butyl hexahydro-3,6-dioxo-1-phenyl-1H-isoindole-4-(3-formyloxypropyl)-3(3H)-carboxylate 
• 848476-42-6 3-((3R,3aR,7R,7aS)-octahydro-1,5-dioxo-3-phenyl-1H-isoindol-7-yl)propyl formate 
• 414871-53-7 (3S,3aS,7aR)-2-(1-methyl-1-phenylethyl)-3-phenyl-2,3,3a,7a-tetrahydro-1H-isoindole-1,5(4H)-dione 
• 268541-14-6 N-benzyl-N-(1-methyl-1-phenylethyl)-4-methoxybenzamide 

Relevant academic research and scientific papers

Synthesis of (±)-kainic acid by dearomatising cyclisation of a lithiated N-benzyl p-anisamide

N-Benzyl p-anisamide 6, on lithiation with Bu(t)Li in the presence of HMPA, undergoes a stereoselective anionic cyclisation with loss of aromaticity to give a bicyclic enone which may be converted in nine steps to (±)-kainic acid.

Ortho-directed functionalization of arenes using magnesate bases

Ortho-directed functionalisation of arenes using lithium alkylmagnesate bases were achieved, demonstrating the potential use of arylmagnesates as suitable arylanions, without a further transmetallation step, for challenging functionalizations such as fluorination, hydroxylation, arylation, vinylation and alkylation through epoxide ring-opening.

The synthesis of (-)-isodomoic acid C

The neuroactive algal metabolite (-)-isodomoic acid C, a kainoid amino acid, has been synthesized for the first time. Asymmetric dearomatizing cyclization of an aromatic amide using a chiral lithium amide base generates a bicyclic enone containing a pyrro

Synthesis of (-)-kainic acid using chiral lithium amides in an asymmetric dearomatizing cyclization

Chiral lithium amide bases are able to deprotonate N-benzyl-N-cumyl anisamides enantioselectively to yield enantiomerically enriched benzylic organolithiums. These spontaneously undergo dearomatising cyclisation to yield, in high enantiomeric excess enantiomerically enriched partially saturated isoindolones, which in some cases may be recrystallised to enantiomeric purity. These isoindolone derivatives are converted in nine steps, among them a surprisingly regioselective Baeyer-Villiger reaction, to (-)-kainic acid.