Diastereo‐ and Enantioselective Michael Addition of 3‐Substituted Oxindoles to Trifluoromethyl‐Substituted Nitro Olefins Catalyzed by a  Cinchona ‐Alkaloid‐Derived Squaramide | Zendy

Zhao MeiXin | Zendy; Ji FeiHu | Zendy; Zhao XiaoLi | Zendy; Han ZeZheng | Zendy; Shi Min | Zendy

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Diastereo‐ and Enantioselective Michael Addition of 3‐Substituted Oxindoles to Trifluoromethyl‐Substituted Nitro Olefins Catalyzed by a Cinchona ‐Alkaloid‐Derived Squaramide

Author(s) -

Zhao MeiXin,

Ji FeiHu,

Zhao XiaoLi,

Han ZeZheng,

Shi Min

Publication year - 2014

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201301457

Subject(s) - squaramide , stereocenter , chemistry , enantioselective synthesis , cinchona , trifluoromethyl , michael reaction , oxindole , nitro , organocatalysis , adduct , catalysis , stereochemistry , organic chemistry , medicinal chemistry , alkyl

Highly efficient diastereo‐ and enantioselective Michael addition reactions between 3‐substituted oxindoles and trifluoromethylated nitro olefins catalyzed by a quinine‐derived squaramide have been investigated. The corresponding adducts, each bearing a chiral tertiary carbon center attached to a trifluoromethyl group and adjacent to a quaternary stereocenter at the C3 position of the oxindole, were obtained in good to excellent yields (up to 99 %) and with high diastereoselectivities (up to >20:1 dr ) and excellent enantioselectivities (up to 99 % ee ).

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