title: Bioinspired intramolecular Diels-Alder reaction: a rapid access to the highly-strained cyclopropane-fused polycyclic skeleton.
abstract: A bioinsipred gold-catalyzed tandem Diels-Alder/Diels-Alder reaction of an enynal and a 1,3-diene, forming the highly-strained benzotricyclo[3.2.1.0(2,7) ]octane skeleton, was reported. In contrast, a Diels-Alder/Friedel-Crafts tandem reaction occurred instead when silver salts were used as the catalyst. Although both reactions experienced the similar Diels-Alder reaction of a pyrylium intermediate with a 1,3-diene, they have different reaction mechanisms. The former proceeded with a stepwise Diels-Alder reaction, while the latter one with a concerted one.
authors: School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640 (P. R. China). zhusf@scut.edu.cn.
authors: Shifa
authors: S
authors: Zhu
authors: Zhengjiang
authors: Z
authors: Guo
authors: Zhipeng
authors: Z
authors: Huang
authors: Huanfeng
authors: H
authors: Jiang
mesh_terms: D002384:Catalysis; D061565:Cycloaddition Reaction; D003521:Cyclopropanes / Q000737:chemistry*; D006046:Gold; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D003521:Cyclopropanes; D011083:Polycyclic Compounds; C000592962:benzotricyclo(3.2.1.0(2,7))octane; D006046:Gold; C030797:cyclopropane
keywords: Diels-Alder reaction; catalysis; cyclopropanes; gold; tandem reactions