Stereoselective Synthesis of 3-Hydroxy-4-arylcyclopentanones and 4-Arylcyclopentenones through a Heck-Matsuda Desymmetrization of meso cis-4-Cyclopentene-1,3-diol

Autor(es)

Carmona, Rafaela C. ^[1] ; Correia, Carlos Roque D. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Estadual Campinas, Inst Quim, UNICAMP, BR-13084971 Campinas, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: ADVANCED SYNTHESIS & CATALYSIS; v. 357, n. 12, p. 2639-2643, AUG 24 2015.
• Citações Web of Science: 17

Resumo

A new palladium-catalyzed route to 3-hydroxy-4-arylcyclopentanones and 4-arylcyclopentenones in a diastereo- and enantioselective manner by a Heck-Matsuda desymmetrization was achieved from the commercially available meso cis-4-cyclopentene-1,3-diol. This method is highly practical, mild, high yielding and is carried out under ``open vessel{''} conditions. Protected and unprotected substrates provide distinct products bearing considerable value as synthetic scaffolds for the synthesis of natural and unnatural bioactive compounds containing a five-membered ring. (AU)

• Processo FAPESP: 11/23832-6 - Novos estudos metodológicos e mecanísticos das reações de arilação de Heck empregando sais de arenodiazônio e aplicações sintéticas
• Beneficiário: Carlos Roque Duarte Correia
• Modalidade de apoio: Auxílio à Pesquisa - Regular
• Processo FAPESP: 13/10183-5 - Arilação de cicloalcenos via reação de Heck-Matsuda assimétrica e aplicações sintéticas
• Beneficiário: Rafaela Costa Carmona
• Modalidade de apoio: Bolsas no Brasil - Doutorado