A polystyrene-supported 9-amino(9-deoxy)epi quinine derivative for continuous flow asymmetric Michael reactions
- 17 February 2015
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Organic & Biomolecular Chemistry
- Vol. 13 (14) , 4204-4209
Abstract
A polystyrene (PS)-supported 9-amino(9-deoxy)epi quinine derivative catalyzes Michael reactions affording excellent levels of conversion and enantioselectivity using different nucleophiles and structurally diverse enones. The highly recyclable, immobilized catalyst has been used to implement a single-pass, continuous flow process (residence time: 40 min) that can be operated for 21 hours without significant decrease in conversion and with improved enantioselectivity with respect to batch operation. The flow process has also been used for the sequential preparation of a small library of enantioenriched Michael adducts.Keywords
This publication has 50 references indexed in Scilit:
- Organocatalytic tandem Michael addition reactions: A powerful access to the enantioselective synthesis of functionalized chromenes, thiochromenes and 1,2-dihydroquinolinesBeilstein Journal of Organic Chemistry, 2012
- Combined bead polymerization and Cinchona organocatalyst immobilization by thiol–ene additionBeilstein Journal of Organic Chemistry, 2012
- A Solid‐Supported Organocatalyst for Continuous‐Flow Enantioselective Aldol ReactionsChemSusChem, 2012
- Recent advances in asymmetric catalysis with cinchona alkaloid-based primary aminesCatalysis Science & Technology, 2011
- Organocatalytic Enantioselective Michael Addition of α-Nitroacetate to α,β-Unsaturated Enones: A Route to Chiral γ-Nitro Ketones and δ-Keto EstersBulletin of the Korean Chemical Society, 2011
- Polymer‐Supported Chiral Organocatalysts: Synthetic Strategies for the Road Towards Affordable Polymeric ImmobilizationEuropean Journal of Organic Chemistry, 2010
- Fast and Enantioselective Production of 1‐Aryl‐1‐propanols through a Single Pass, Continuous Flow ProcessAdvanced Synthesis & Catalysis, 2008
- 9-Thiourea Cinchona alkaloid supported on mesoporous silica as a highly enantioselective, recyclable heterogeneous asymmetric catalystChemical Communications, 2008
- Cross-coupling reactions in Cinchona alkaloid chemistry: aryl-substituted and dimeric quinine, quinidine, as well as quincorine and quincoridine derivativesJournal of the Chemical Society, Perkin Transactions 1, 2001
- Asymmetric Induction in the Base-Catalyzed Reactions Using Polymer-Supported Quinines with Spacer GroupsBulletin of the Chemical Society of Japan, 1987