Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 43, Pages 17885-17888Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja308858y
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Funding
- Swiss National Science Foundation
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A domino inverse electron-demand Diels-Alder (IEDDA)/cyclopropanation reaction of diazines was discovered by applying electron-rich furans in the bidentate Lewis acid catalyzed IEDDA reaction. This process produces benzonorcaradienes in excellent yields with a low loading of a bidentate Lewis acid catalyst of 2 to 5 mol %. We demonstrate the broad applicability by 20 examples with different dienophiles and a variety of dienes. A detailed mechanism is proposed supported by DFT calculations.
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