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Rapid Access to 2‐Methylene Tetrahydrofurans and γ‐Lactones: A Tandem Four‐Step Process
Author(s) -
Liang Renxiao,
Chen Kai,
Zhang Qiaohui,
Zhang Jiantao,
Jiang Huanfeng,
Zhu Shifa
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201511133
Subject(s) - knoevenagel condensation , tandem , methylene , chemistry , atom economy , hydrolysis , combinatorial chemistry , organic chemistry , catalysis , materials science , composite material
Abstract A one‐pot tandem process involving hydrolysis, Knoevenagel condensation, Michael addition, and Conia‐ene (HKMC) reactions has been developed for the rapid synthesis of indanone‐fused 2‐methylene tetrahydrofurans from the reaction of enynals and propynols. In this process, two rings and four bonds are generated with 100 % atom‐economy and high step‐efficiency. The resulting tetrahydrofurans were readily oxidized into α‐methylene γ‐lactones, which are one of the most important substructures in natural and bioactive compounds.