Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 42, 2015
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Article information


Submitted
02 Jul 2015
Accepted
25 Aug 2015
First published
26 Aug 2015

Org. Biomol. Chem., 2015,13, 10569-10577
Article type
Paper
Author version available

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

Social activity

Search articles by author

Spotlight

Advertisements