A new, chiral aminoanthracene for the Diels–Alder/retro-Diels–Alder sequence in lactam and butenolide synthesis

9-(2-Phenylethyl)aminoanthracene has been prepared and used as a template in the Diels–Alder/retro-Diels–Alder sequence to produce α,β-butenolides and α,β-unsaturated lactams. In this sequence the aminoanthracene serves as a stereo- and regiocontrolling chaperone in guiding maleic anhydride or N-alkylmaleimides through transformations to the butenolide or lactam targets.