Remarkable Electronic Effect on the Diastereoselectivity of the Heck Reaction of Methyl Cinnamate with Arenediazonium Salts: Formal Total Synthesis of (+/-)-Indatraline and (+/-)-Sertraline

Autor(es)

Pastre, Julio Cezar ^[1] ; Duarte Correia, Carlos Roque ^[1]

Afiliação do(s) autor(es)

^[1] Univ Estadual Campinas, UNICAMP, Inst Quim, BR-13083970 Campinas, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: ADVANCED SYNTHESIS & CATALYSIS; v. 351, n. 9, p. 1217-1223, JUN 2009.
• Citações Web of Science: 51

Resumo

An efficient and stereoselective protocol for the preparation of beta,beta-disubstituted acrylates in good to high yields by means of a Heck-Matsuda arylation was accomplished. The method employs a base- and ligand-free Heck arylation reaction of methyl cinnamate using both electron-deficient and electron-rich arenediazonium salts as electrophiles. The Heck reaction displays a remarkable electronic dependence regarding the diastereoselectivity of the arylation process, which correlates with the electronic nature of the arenediazonium salts employed. A rationale for the observed diastereoselectivity is presented. The overall methodology provides a convenient route to 3-arylindanones and 4-aryltetralones allowing the concise formal total syntheses of the therapeutically important psychoactive compounds (+/-)-indatraline and (+/-)-sertraline. (AU)

• Processo FAPESP: 05/01614-6 - Novos desafios e aplicacoes da reacao de avaliacao de heck empregando sais de diazonio.
• Beneficiário: Júlio Cezar Pastre
• Modalidade de apoio: Bolsas no Brasil - Doutorado