Chiral Squaramide-Catalyzed Highly Enantioselective Michael Addition of 2-Hydroxy-1,4-naphthoquinones to Nitroalkenes

• Published in: Advanced synthesis & catalysis Vol. 353; no. 8; pp. 1241 - 1246
• Main Authors: Yang, Wen, Du, Da-Ming
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.05.2011; WILEY‐VCH Verlag; Wiley; Wiley-VCH
• Subjects: Alicyclic compounds; Alicyclic compounds, terpenoids, prostaglandins, steroids; asymmetric catalysis; Asymmetry; Catalysis; Catalysts; Catalysts: preparations and properties; Chemistry; Chemistry, Applied; Chemistry, Organic; Condensed benzenic and aromatic compounds; Exact sciences and technology; General and physical chemistry; Michael addition; Michael reaction; naphthoquinones; nitroalkenes; Noncondensed benzenic compounds; Organic chemistry; organocatalysis; Physical Sciences; Preparations and properties; Science & Technology; squaramides; Synthesis; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; Michael addition; squaramides; nitroalkenes; DESIGN; DONORS; asymmetric catalysis; organocatalysis; ORGANOCATALYSTS; 1,4-NAPHTHOQUINONE DERIVATIVES; NITROOLEFINS; naphthoquinones; AGENTS; ANTIFUNGAL; CONJUGATE ADDITION; Nitro compound; Catalytic reaction; Enantioselectivity; I naphthoquinones; Quinone; Naphthoquinone derivatives; Chiral compound; Asymmetric catalysis; Functionalization; Asymmetric synthesis; Enantiomeric excess; Aromatic compound; Chemical synthesis; Catalyst; Ethylenic compound
• ISSN: 1615-4150; 1615-4169; 1615-4169
• DOI: 10.1002/adsc.201000981

A chiral squaramide‐organocatalyzed, highly enantioselective Michael addition of 2‐hydroxy‐1,4‐naphthoquinones to nitroalkenes has been developed. This reaction afforded the chiral naphthoquinones in excellent yields (up to 99%) and excellent enantioselectivity (up to 98% ee) under very low catalyst loading (0.25 mol%). This organocatalytic asymmetric Michael addition provides an efficient alternative route toward the synthesis of chiral functionalized naphthoquinones.