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Stereoselective synthesis of densely functionalized pyrrolidin-2-ones by a conjugate addition/nitro-Mannich/lactamization reaction.

Anderson, JC; Horsfall, LR; Kalogirou, AS; Mills, MR; Stepney, GJ; Tizzard, GJ; (2012) Stereoselective synthesis of densely functionalized pyrrolidin-2-ones by a conjugate addition/nitro-Mannich/lactamization reaction. J Org Chem , 77 (14) 6186 - 6198. 10.1021/jo301000r.

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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.

Type:Article
Title:Stereoselective synthesis of densely functionalized pyrrolidin-2-ones by a conjugate addition/nitro-Mannich/lactamization reaction.
Location:United States
DOI:10.1021/jo301000r
Language:English
Keywords:Catalysis, Copper, Molecular Structure, Nitro Compounds, Organometallic Compounds, Pyrrolidinones, Stereoisomerism, Zinc
UCL classification:UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry

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