Adaptation of a Small-Molecule Hydrogen-Bond DonorCatalyst to an Enantioselective Hetero-Diels–Alder ReactionHypothesized for Brevianamide Biosynthesis

摘要

Chiral diamine-derived hydrogen-bond donors were evaluated for their ability to effect stereocontrol in an intramolecular hetero-Diels–Alder (HDA) reaction hypothesized in the biosynthesis of brevianamides A and B. Collectively, these results provide proof of principle that small-molecule hydrogen-bond catalysis, if even based on a hypothetical biosynthesis construct, holds significant potential within enantioselective natural product synthesis.