190774-35-7

Upstream product

• 190774-33-5 (S)-N-(4-methylpent-3-enyl)phenylglycine methyl ester 
• 6591-61-3 (S)-Phenylglycine methyl ester 
• 2270-59-9 1-bromo-4-methylpent-3-ene 
• 190774-34-6 (S)-N-benzyl-N-(4-methylpent-3-enyl)phenylglycine methyl ester 

Downstream Products

• 190774-36-8 (S)-[Benzyl-(4-methyl-pent-3-enyl)-amino]-phenyl-acetaldehyde 

Relevant academic research and scientific papers

Enantioselective approach towards potential substance P antagonists via hetero-ene reaction of phenylglycine derivatives

Phenylglycine methyl ester 7 can be converted in a four-step sequence to the aldehyde 11. Lewis acid catalyzed hetero-ene reaction of 11 gave a mixture of 3-hydroxy-2-phenylpiperidines 14a,b with high diastereoselectivity. The major diastereomer 14a was further transformed into 4-isopropyl-3-(2-methoxybenzylamino)-2-phenylpiperidine (19), a compound structurally related to a substance P antagonist, in five steps via azide displacement and reductive amination.