1383958-33-5Relevant academic research and scientific papers
Stereoselective synthesis of densely functionalized pyrrolidin-2-ones by a conjugate addition/nitro-mannich/lactamization reaction
Anderson, James C.,Horsfall, Lisa R.,Kalogirou, Andreas S.,Mills, Matthew R.,Stepney, Gregory J.,Tizzard, Graham J.
, p. 6186 - 6198 (2012)
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.
