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Bioinspired Intramolecular Diels–Alder Reaction: A Rapid Access to the Highly‐Strained Cyclopropane‐Fused Polycyclic Skeleton
Author(s) -
Zhu Shifa,
Guo Zhengjiang,
Huang Zhipeng,
Jiang Huanfeng
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201304839
Subject(s) - diels–alder reaction , intramolecular force , diene , chemistry , cyclopropane , stepwise reaction , tandem , catalysis , cycloaddition , photochemistry , medicinal chemistry , organic chemistry , ring (chemistry) , materials science , order of reaction , natural rubber , physics , quantum mechanics , reaction rate constant , kinetics , composite material
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.