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Atom-economic synthesis of cyclobuta[a]naphthalen-4-ols via a base-promoted [2 + 2] cycloaddition/1,6-nucleophilic addition cascade

Authors :
Feng-Lie Xie
Jia-Yin Wang
You-Jian Wang
Jian-Qiang Hu
Shi-Zhao Yang
Shu-Jiang Tu
Bo Jiang
Wen-Juan Hao
Source :
Organicbiomolecular chemistry. 16(39)
Publication Year :
2018

Abstract

A first atom-economic [2 + 2] cycloaddition/1,6-conjugate addition cascade of yne-allenones with C-nucleophiles including 1,3-dicarbonyls and α,α-dicyanoolefins under base-promoted conditions has been established, enabling the direct construction of C(sp3)–C(sp3) bonds to generate cyclobuta[a]naphthalen-1-ols with generally good yields. These resulting products have a cyclobutene unit that contains both an aryl and alkyl group.

Details

ISSN :
14770539
Volume :
16
Issue :
39
Database :
OpenAIRE
Journal :
Organicbiomolecular chemistry
Accession number :
edsair.doi.dedup.....9faf5417cd010ad942aa8922084c5e5b