4.8 Article

Weak Bronsted Acid-Thiourea Co-catalysis: Enantioselective, Catalytic Protio-Pictet-Spengler Reactions

Journal

ORGANIC LETTERS
Volume 11, Issue 4, Pages 887-890

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol802887h

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Funding

  1. NIH [GM-43214]

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The development of one-pot imine formation and asymmetric Pictet-Spengler reactions cocatalyzed by a chiral thiourea and benzoic acid is described. Optically active tetrahydro-beta-carbolines, ubiquitous structural motifs in biologically active natural products, are obtained in high ee directly from tryptamine and aldehyde precursors.

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