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

Ramadan Ali Bawa | Zendy; FrancoisMoana Gautier | Zendy; Harry Adams | Zendy; Anthony J. H. M. Meijer | Zendy; Simon Jones | Zendy

Open Access

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

Author(s) -

Ramadan Ali Bawa,

FrancoisMoana Gautier,

Harry Adams,

Anthony J. H. M. Meijer,

Simon Jones

Publication year - 2015

Publication title -

organic and biomolecular chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.923

H-Index - 146

eISSN - 1477-0539

pISSN - 1477-0520

DOI - 10.1039/c5ob01343g

Subject(s) - anthracene , chemistry , cycloaddition , stereoselectivity , selectivity , hydrogen bond , diels–alder reaction , hydrogen , computational chemistry , medicinal chemistry , organic chemistry , molecule , catalysis

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.

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