Direct Synthesis of Highly Substituted Cyclopentadienes and Derivatives from the Self-Condensation of Renewable Ethyl Levulinate

Autor(es)

Santos, Camila S. ^[1] ; Burtoloso, Antonio C. B. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Sao Paulo, Chem Inst Sao Carlos, BR-13560970 Sao Paulo, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY; v. 2018, n. 45, p. 6350-6354, DEC 6 2018.
• Citações Web of Science: 1

Resumo

Tri-substituted cyclopentadienes and cyclopentanes, high-value-added compounds, are readily prepared from ethyl levulinate, a chemical platform easily obtained from biomass. Key steps involve coupling two molecules of ethyl levulinate in the presence of pyrrolidine, followed by a base-catalyzed intramolecular aldol condensation, to provide a singly-purified and easily derivatizable cyclopentadiene in almost 40 % isolated overall yield. Reaction conditions are mild, simple and employ green solvents such as ethanol and anisole. This method opens a new pathway to preparing complex molecules from renewable feedstocks. (AU)

• Processo FAPESP: 17/23329-9 - Síntese de ciclopentanos substituídos e polióis de cadeia longa a partir de plataformas químicas abundantes e oriundas da biomassa
• Beneficiário: Antonio Carlos Bender Burtoloso
• Linha de fomento: Auxílio à Pesquisa - Regular