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Start Over Author "Klausen RS" Journal organic letters
2 results on '"Klausen RS"'

1. Thiourea-catalyzed enantioselective iso-Pictet-Spengler reactions.

Author

Lee Y, Klausen RS, and Jacobsen EN

Subjects
Carbolines chemistry, Catalysis, Combinatorial Chemistry Techniques, Molecular Structure, Stereoisomerism, Aldehydes chemistry, Benzoic Acid chemistry, Carbolines chemical synthesis, Thiourea chemistry, Tryptamines chemistry
Abstract

A one-pot condensation of isotryptamines and aldehydes that affords enantiomerically enriched 4-substituted tetrahydro-γ-carbolines is reported. The reaction is induced by a chiral thiourea/benzoic acid dual catalyst system. Purification of the N-Boc-protected products by trituration or crystallization provides the optically pure tetrahydro-γ-carboline derivatives in a scalable and highly practical procedure., (© 2011 American Chemical Society)

Published
2011
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2. Weak Brønsted acid-thiourea co-catalysis: enantioselective, catalytic protio-Pictet-Spengler reactions.

Author

Klausen RS and Jacobsen EN

Subjects
Benzoic Acid chemistry, Carbolines chemistry, Catalysis, Cyclization, Imines chemistry, Indole Alkaloids chemical synthesis, Molecular Structure, Stereoisomerism, Thiourea chemistry, Benzaldehydes chemistry, Carbolines chemical synthesis, Thiourea analogs & derivatives, Tryptamines chemistry
Abstract

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.

Published
2009
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