Cyclopentadienone Formation from β,γ-Unsaturated Cyclopentenones and Its Application in Diels–Alder Reactions

We
report that α-acyloxy-β,γ-unsaturated cyclopentenones
were used as starting substrates to make various trisubstituted cyclopentadienones.
The substrates are easily available in one step from our previously
developed protocol, and the potential of this cyclopentadienone formation
method was demonstrated in a series of Diels–Alder reactions,
forming dimerization products, dimethyl phthalate derivatives, and
polyaryl benzene compounds.

本研究报道，以α-酰氧基-β,γ-不饱和环戊烯酮（α-acyloxy-β,γ-unsaturated cyclopentenones）为起始底物，可制备多种三取代环戊二烯酮。该底物可通过本课题组此前开发的一步法方案便捷获得，本研究通过一系列狄尔斯-阿尔德（Diels–Alder）反应验证了该环戊二烯酮合成方法的应用潜力，所得产物包括二聚产物、邻苯二甲酸二甲酯衍生物以及多芳基苯化合物。