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Enantioselective Michael Addition of Nitroalkanes to Nitroalkenes Catalyzed by Chiral Bifunctional Quinine‐Based Squaramides
Author(s) -
Kanberoğlu Esra,
Tanyeli Cihangir
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500339
Subject(s) - squaramide , bifunctional , chemistry , michael reaction , enantioselective synthesis , organocatalysis , conjugate , catalysis , adduct , steric effects , addition reaction , organic chemistry , combinatorial chemistry , medicinal chemistry , mathematical analysis , mathematics
A family of chiral bifunctional acid‐/base‐type quinine/squaramide organocatalysts is shown to be highly active promoters of the conjugate addition of 1‐nitropropane to various trans‐ β‐nitroalkenes. The cooperation of the quinine and the sterically encumbered squaramide moieties catalyzed the Michael addition reactions at 0 °C by using a catalyst loading of only 2 mol % to afford the 1,3‐dinitro Michael adducts with excellent enantioselectivity and diastereoselectivity (up to 95 % ee and syn / anti isomers up to 96:4).