A Catalytic Reactor for the Organocatalyzed Enantioselective Continuous Flow Alkylation of Aldehydes. Issue 12 (21st October 2014)

• Record Type: Journal Article
• Authors: Porta, Riccardo; Benaglia, Maurizio; Puglisi, Alessandra; Mandoli, Alessandro; Gualandi, Andrea; Cozzi, Pier Giorgio
• Is Part Of: ChemSusChem. Volume 7:Issue 12(2014:Dec.)
• Page Start: 3534
• Page End: 3540
• Publication Date: 2014-10-21
• Subjects: Green chemistry -- Periodicals; Sustainable engineering -- Periodicals; Chemistry -- Periodicals; Chemical engineering -- Periodicals; 660
• DOI: 10.1002/cssc.201402610
• Languages: English
• ISSNs: 1864-5631

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The use of immobilized metal‐free catalysts offers the unique possibility to develop sustainable processes in flow mode. The challenging intermolecular organocatalyzed enantioselective alkylation of aldehydes was performed for the first time under continuous flow conditions. By using a packed‐bed reactor filled with readily available supported enantiopure imidazolidinone, different aldehydes were treated with three distinct cationic electrophiles. In the organocatalyzed α‐alkylation of aldehydes with 1, 3‐benzodithiolylium tetrafluoroborate, excellent enantioselectivities, in some cases even better than those obtained in the flask process (up to 95 % <italic>ee</italic> at 25 °C), and high productivity (more than 3800 h⁻¹) were obtained, which thus shows that a catalytic reactor may continuously produce enantiomerically enriched compounds. Treatment of the alkylated products with Raney‐nickel furnished enantiomerically enriched α‐methyl derivatives, key intermediates for active pharmaceutical ingredients and natural products.</p> </abstract>