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Issue 42, 2015
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Evaluating hydrogen bonding control in the diastereoselective Diels–Alder reactions of 9-(2-aminoethyl)-anthracene derivatives

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Abstract

Several 9-(2-aminoethyl)anthracene derivatives were prepared with different nitrogen substitutents including alkyl, acetamide, trifluoroacaeamide and t-butyl carbamate. The selectivity in Diels–Alder cyclodaddition reaction with N-methyl maleimide was evaluated through single crystal X-ray analysis of the products. Models for the change in selectivity with hydrogen bond acceptor are proposed, supported by DFT level calculations.

Graphical abstract: Evaluating hydrogen bonding control in the diastereoselective Diels–Alder reactions of 9-(2-aminoethyl)-anthracene derivatives

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Publication details

The article was received on 02 Jul 2015, accepted on 25 Aug 2015 and first published on 26 Aug 2015


Article type: Paper
DOI: 10.1039/C5OB01343G
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Citation: Org. Biomol. Chem., 2015,13, 10569-10577
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    Evaluating hydrogen bonding control in the diastereoselective Diels–Alder reactions of 9-(2-aminoethyl)-anthracene derivatives

    R. A. Bawa, F.-M. Gautier, H. Adams, A. J. H. M. Meijer and S. Jones, Org. Biomol. Chem., 2015, 13, 10569
    DOI: 10.1039/C5OB01343G

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