Direct enantioselective Bronsted acid catalyzed N-acyliminium cyclization cascades of tryptamines and ketoacids.

Journal article

A direct enantio- and diastereoselective N-acyliminium cyclization cascade through chiral phosphoric acid catalyzed condensation of tryptamines with γ- and δ-ketoacid derivatives to provide architecturally complex heterocycles has been developed. The reaction is technically simple to perform, atom-efficient, and broad in scope. Employing 10 mol % of (R)-BINOL derived chiral phosphoric acids in refluxing toluene allowed the polycyclic product materials to be generated in good yields (53-99%) and moderate to high enantioselectivities (68-98% ee).

Authors: Holloway, C; Muratore, M; Storer, R; Dixon, D

• Publication status: Published
• Journal: Organic letters
• Volume: 12
• Issue: 21
• Pages: 4720-4723
• Publication date: 2010-11-01
• DOI: 10.1021/ol101651t
• EISSN: 1523-7052
• ISSN: 1523-7060
• Language: English
• Keywords: Molecular Structure; Stereoisomerism; Imines; Acylation; Cyclization; Acids; Catalysis; Tryptamines