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Thiourea-Catalyzed Enantioselective Iso-Pictet-Spengler Reactions

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2011

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American Chemical Society
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Lee, Yunmi, Rebekka S. Klausen, and Eric N. Jacobsen. 2011. Thiourea-catalyzed enantioselective Iso-Pictet Spengler reactions. Organic Letters 13(20): 5564-5567.

Abstract

A one-pot condensation of isotryptamines and aldehydes that affords enantiomerically enriched 4-substituted tetrahydro-(\gamma)-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-(\gamma)-carboline derivatives in a scalable and highly practical procedure.

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