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Direct Synthesis of Highly Substituted Cyclopentadienes and Derivatives from the Self‐Condensation of Renewable Ethyl Levulinate
Author(s) -
Santos Camila S.,
Burtoloso Antonio C. B.
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801197
Subject(s) - chemistry , anisole , organic chemistry , intramolecular force , aldol condensation , molecule , yield (engineering) , catalysis , materials science , metallurgy
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.