A polystyrene-supported 9-amino(9-deoxy)epi quinine derivative for continuous flow asymmetric Michael reactions. Issue 14 (27th February 2015)

• Record Type: Journal Article
• Authors: Izquierdo, Javier; Ayats, Carles; Henseler, Andrea H.; Pericàs, Miquel A.
• Is Part Of: Organic & biomolecular chemistry. Volume 13:Issue 14(2015)
• Page Start: 4204
• Page End: 4209
• Publication Date: 2015-02-27
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c5ob00325c
• Languages: English
• ISSNs: 1477-0520

Abstract

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 under continuous flow conditions. 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.