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Synfacts 2009(4): 0443-0443
DOI: 10.1055/s-0028-1088101
DOI: 10.1055/s-0028-1088101
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Brønsted Acid-Thiourea Co-Catalysis
R. S. Klausen, E. N. Jacobsen*
Harvard University, Cambridge, USA
Further Information
Publication History
Publication Date:
23 March 2009 (online)
Significance
The thiourea-1 Brønsted acid co-catalyzed Pictet-Spengler reaction of various tryptamines and aldehydes is reported. The authors assume the transformation to proceed via Brønsted acid supported Brønsted acid catalysis (I). After formation of an iminium ion intermediate, the enantioselective, chiral counteranion-assisted cyclization occurs. Subsequent rearomatization liberates the product and the catalysts.