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Issue 28, 2014
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Unusual regio- and stereo-selectivity in Diels–Alder reactions between bulky N-phenylmaleimides and anthracene derivatives

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Abstract

Unusual regio- and stereo-selectivity in Diels–Alder (D–A) reactions were achieved between bulky N-phenylmaleimides and anthracene derivatives. Using multiple substituents with steric hindrance on both diene and dienophile, a noticeable shift toward 1,4-addition was successfully obtained. The substrate scope in this reaction was broad and the highest yield of anti-1,4-adducts was over 90%. Novel structures of anti-1,4-adducts were confirmed by single crystal X-ray diffraction analysis. This study not only provides the first reported method of synthesizing anti-1,4-adducts and achieving otherwise unattainable regio- and stereo-selectivity, but also elucidates the importance of combining the steric effects of two reactants to shift products toward 1,4-adducts. Moreover, the resulting 1,4-adducts could be further functionalized through their halogen groups via carbon–carbon coupling reactions.

Graphical abstract: Unusual regio- and stereo-selectivity in Diels–Alder reactions between bulky N-phenylmaleimides and anthracene derivatives

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Publication details

The article was received on 21 May 2014, accepted on 03 Jun 2014 and first published on 03 Jun 2014


Article type: Communication
DOI: 10.1039/C4OB01052C
Citation: Org. Biomol. Chem., 2014,12, 5102-5107
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    Unusual regio- and stereo-selectivity in Diels–Alder reactions between bulky N-phenylmaleimides and anthracene derivatives

    H. Chen, E. Yao, C. Xu, X. Meng and Y. Ma, Org. Biomol. Chem., 2014, 12, 5102
    DOI: 10.1039/C4OB01052C

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