Organocatalytic Asymmetric Michael Addition of Oxindoles to Nitroolefins for the Synthesis of 2,2-Disubstituted Oxindoles Bearing Adjacent Quaternary and Tertiary Stereocenters

• Published in: Journal of organic chemistry Vol. 77; no. 24; pp. 11307 - 11312
• Main Authors: Jin, Cheng-Yong, Wang, Yao, Liu, Yao-Zong, Shen, Chao, Xu, Peng-Fei
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 21.12.2012; Amer Chemical Soc
• Subjects: Alkenes - chemistry; Catalysis; Catalysts: preparations and properties; Chemistry; Chemistry Techniques, Synthetic; Chemistry, Organic; Exact sciences and technology; General and physical chemistry; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Indoles - chemical synthesis; Indoles - chemistry; Nitro Compounds - chemistry; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Stereoisomerism; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; ROUTE; 1,3-DICARBONYL COMPOUNDS; MANNICH REACTIONS; DERIVATIVES; HIGHLY EFFICIENT; NITROALKENES; CATALYSTS; Michael addition; Nitro compound; Catalytic reaction; Nitrogen heterocycle; Organocatalyst; Bifunctional compound; Lactam; Chiral compound; Thioureas; Indoline derivative; Stereoselectivity; Asymmetric synthesis; Indole derivatives; Chemical synthesis
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo301886j

A bifunctional thiourea-catalyzed Michael addition of activated indolin-3-ones to nitroolefins has been developed. The synthetically useful 2,2-disubstituted indolin-3-one derivatives with vicinal chiral quaternary–tertiary stereocenters were obtained in high yields with excellent stereoselectivities. The adduct can be readily transformed into a structurally interesting heterocyclic architecture by means of further synthetic elaboration.