Evaluating hydrogen bonding control in the diastereoselective Diels–Alder reactions of 9-(2-aminoethyl)-anthracene derivatives. Issue 42 (4th September 2015)

• Record Type: Journal Article
• Authors: Bawa, R. A.; Gautier, F.-M.; Adams, H.; Meijer, A. J. H. M.; Jones, S.
• Is Part Of: Organic & biomolecular chemistry. Volume 13:Issue 42(2015)
• Page Start: 10569
• Page End: 10577
• Publication Date: 2015-09-04
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c5ob01343g
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Hydrogen bonding can be used to control the stereoselectivity of the cycloaddition of some anthracene derivatives. DFT calculations provide support for the origins of the selectivity in these reactions. 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.