Bioinspired Intramolecular Diels–Alder Reaction: A Rapid Access to the Highly‐Strained Cyclopropane‐Fused Polycyclic Skeleton. Issue 9 (5th February 2014)

• Record Type: Journal Article
• Authors: Zhu, Shifa; Guo, Zhengjiang; Huang, Zhipeng; Jiang, Huanfeng
• Is Part Of: Chemistry. Volume 20:Issue 9(2014)
• Page Start: 2425
• Page End: 2430
• Publication Date: 2014-02-05
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201304839
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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.</p> </abstract>