Weak Brønsted Acid−Thiourea Co-catalysis: Enantioselective, Catalytic Protio-Pictet−Spengler Reactions
- 29 January 2009
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 11 (4) , 887-890
- https://doi.org/10.1021/ol802887h
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-β-carbolines, ubiquitous structural motifs in biologically active natural products, are obtained in high ee directly from tryptamine and aldehyde precursors.Keywords
This publication has 17 references indexed in Scilit:
- Enantioselective Thiourea-Catalyzed Additions to Oxocarbenium IonsJournal of the American Chemical Society, 2008
- Cooperative Brønsted Acid-Type Organocatalysis: Alcoholysis of Styrene OxidesOrganic Letters, 2008
- Strictosidine Synthase: Mechanism of a Pictet−Spengler Catalyzing EnzymeJournal of the American Chemical Society, 2007
- Indium‐Mediated Asymmetric Allylation of Acylhydrazones Using a Chiral Urea CatalystAngewandte Chemie International Edition in English, 2007
- Asymmetric Catalysis by Chiral Hydrogen‐Bond DonorsAngewandte Chemie International Edition in English, 2006
- Catalytic Asymmetric Pictet−Spengler ReactionJournal of the American Chemical Society, 2006
- Stereocontrolled Total Synthesis of (−)-Eudistomin CJournal of the American Chemical Society, 2005
- Highly Enantioselective Catalytic Acyl-Pictet−Spengler ReactionsJournal of the American Chemical Society, 2004
- Chiral Lewis Acid-Mediated Enantioselective Pictet−Spengler Reaction of Nb-Hydroxytryptamine with AldehydesThe Journal of Organic Chemistry, 1998
- The Pictet-Spengler condensation: a new direction for an old reactionChemical Reviews, 1995