Stereoselective Synthesis of Densely Functionalized Pyrrolidin-2-ones by a Conjugate Addition/Nitro-Mannich/Lactamization Reaction
Citations Over TimeTop 10% of 2012 papers
Abstract
Copper-catalyzed conjugate addition of diorgano zinc reagents to nitroacrylate 1 followed by a subsequent nitro-Mannich reaction and in situ lactamization leads to an efficient one-pot synthesis of 1,3,5-trisubstituted 4-nitropyrrolidin-2-ones (5). The versatility of the reaction is shown for a wide range of N-p-(methoxy)phenyl protected aldimines 3 derived from alkyl, aryl, and heteroaryl aldehydes. The densely functionalized pyrrolidin-2-ones 5 are isolated as single diastereoisomers (40 examples, 33-84% yield). An enantioselective copper-catalyzed conjugate addition of diethylzinc led to highly crystalline products that could be recrystallized to enantiopurity in high yield. A range of successful chemoselective transformations were investigated, which widens the applicability of the pyrrolidn-2-ones as stereochemically pure building blocks for further organic synthesis.
Related Papers
- → Studies of Reversible Conjugate Additions(2013)61 cited
- → Short and stereoselective synthesis of manzacidins A and C, and their enantiomers(2008)16 cited
- → UO‐Catalyzed Oligothioadenylate Synthesis with High Regio‐ and Stereoselectivity(1993)25 cited
- → Stereoselective synthesis of (±)-ancistrofuran: stereoselective reduction of a γ-hydroxyketone(1984)14 cited
- → Catalyst-Controlled Stereoselective Construction of Indole-Fused Heterocycles through Cycloadditions of Indolyl-Allenes: A Theoretical Investigation(2021)