Thiourea-Catalyzed Enantioselective Iso-Pictet–Spengler Reactions

Thiourea-Catalyzed Enantioselective Iso-Pictet–Spengler Reactions

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 crystallizat...

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Veröffentlicht in:Organic letters 2011-10, Vol.13 (20), p.5564-5567
Hauptverfasser: Lee, Yunmi, Klausen, Rebekka S, Jacobsen, Eric N
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes - chemistry
Benzoic Acid - chemistry
Carbolines - chemical synthesis
Carbolines - chemistry
Catalysis
Combinatorial Chemistry Techniques
Molecular Structure
Stereoisomerism
Thiourea - chemistry
Tryptamines - chemistry
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol202300t