Chiral Squaramide-Catalyzed Highly Enantioselective Michael Addition of 2-Hydroxy-1,4-naphthoquinones to Nitroalkenes
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...
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| Published in | Advanced synthesis & catalysis Vol. 353; no. 8; pp. 1241 - 1246 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
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Weinheim
WILEY-VCH Verlag
01.05.2011
WILEY‐VCH Verlag Wiley Wiley-VCH |
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| Abstract | 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. |
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| AbstractList | 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. 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. 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[FormulaOmitted]mol%). This organocatalytic asymmetric Michael addition provides an efficient alternative route toward the synthesis of chiral functionalized naphthoquinones. |
| Author | Du, Da-Ming Yang, Wen |
| Author_xml | – sequence: 1 givenname: Wen surname: Yang fullname: Yang, Wen organization: School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081, People's Republic of China, Fax: (+86)-010-6891-4985 – sequence: 2 givenname: Da-Ming surname: Du fullname: Du, Da-Ming email: dudm@bit.edu.cn organization: School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081, People's Republic of China, Fax: (+86)-010-6891-4985 |
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| Keywords | 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 |
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| Snippet | A chiral squaramide‐organocatalyzed, highly enantioselective Michael addition of 2‐hydroxy‐1,4‐naphthoquinones to nitroalkenes has been developed. This... A chiral squaramide-organocatalyzed, highly enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes has been developed. This... |
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| SubjectTerms | 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 |
| Title | Chiral Squaramide-Catalyzed Highly Enantioselective Michael Addition of 2-Hydroxy-1,4-naphthoquinones to Nitroalkenes |
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