Enantio- and diastereoselective conjugate borylation/Mannich cyclization. Issue 22 (21st May 2020)

• Record Type: Journal Article
• Authors: Larin, Egor M.; Loup, Joachim; Polishchuk, Iuliia; Ross, Rachel J.; Whyte, Andrew; Lautens, Mark
• Is Part Of: Chemical science. Volume 11:Issue 22(2020)
• Page Start: 5716
• Page End: 5723
• Publication Date: 2020-05-21
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d0sc02421j
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : Copper-catalyzed enantio- and diastereoselective conjugate borylation across Michael acceptors, with subsequent Mannich-type cyclization, was utilized to construct tetrahydroquinoline scaffolds containing three contiguous stereocenters. Abstract : Strategies to capitalize on enolate intermediates generated from stereoselective conjugate borylation to α, β-unsaturated carbonyl systems are surprisingly rare despite the ubiquity of Michael acceptors, and the potential to generate valuable scaffolds bearing multiple stereocenters. Herein, we report a mild and stereoselective copper-catalyzed conjugate borylation/Mannich cyclization reaction. This strategy is feasible with a broad range of Michael acceptors, and can be leveraged to generate versatile borylated tetrahydroquinoline scaffolds bearing three contiguous stereocenters. The synthetic potential of these complex heterocycles has been explored through a series of derivatization studies.