Highly Enantioselective Synthesis of Indolines: Asymmetric Hydrogenation at Ambient Temperature and Pressure with Cationic Ruthenium Diamine Catalysts
- 30 September 2016
- journal article
- research article
- Published by Wiley in Angewandte Chemie International Edition
- Vol. 55 (44) , 13863-13866
Abstract
A highly enantioselective synthesis of indolines by asymmetric hydrogenation of 1H‐indoles and 3H‐indoles at ambient temperature and pressure, catalyzed by chiral phosphine‐free cationic ruthenium complexes, has been developed. Excellent enantio‐ and diastereoselectivities (up to >99 % ee, >20:1 d.r.) were obtained for a wide range of indole derivatives, including unprotected 2‐substituted and 2,3‐disubstituted 1H‐indoles, as well as 2‐alkyl‐ and 2‐aryl‐substituted 3H‐indoles.Keywords
This publication has 83 references indexed in Scilit:
- Total Synthesis of Indoline Alkaloids: A Cyclopropanation StrategyAccounts of Chemical Research, 2011
- (S)‐Indoline‐3‐Carboxylic Acid: A New Organocatalyst for the Anti Mannich‐Type ReactionChemCatChem, 2010
- Asymmetric Total Synthesis of VindolineJournal of the American Chemical Society, 2010
- Tetrazolic Acid Functionalized Dihydroindol: Rational Design of a Highly Selective Cyclopropanation OrganocatalystThe Journal of Organic Chemistry, 2007
- Pharmacological Profile of the 5‐HT2C Receptor Agonist WAY‐163909; Therapeutic Potential in Multiple IndicationsCNS Drug Reviews, 2006
- Synthesis of two (S)-indoline-based chiral auxiliaries and their use in diastereoselective alkylation reactionsTetrahedron: Asymmetry, 2006
- Malagashanine potentiates chloroquine antimalarial activity in drug resistant Plasmodium malaria by modifying both its efflux and influxMolecular and Biochemical Parasitology, 2006
- Enantioselective Organocatalytic Cyclopropanations. The Identification of a New Class of Iminium Catalyst Based upon Directed Electrostatic ActivationJournal of the American Chemical Society, 2005
- Indoline and piperazine containing derivatives as a novel class of mixed D2/D4 receptor antagonists. Part 1: Identification and structure–activity relationshipsBioorganic & Medicinal Chemistry Letters, 2002
- Total Synthesis of (+)-Aspidospermidine: A New Strategy for the Enantiospecific Synthesis of Aspidosperma AlkaloidsJournal of the American Chemical Society, 2002