Enantioselective Michael Addition of Nitroalkanes to Nitroalkenes Catalyzed by Chiral Bifunctional Quinine-Based Squaramides

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--nitroalkenes. The cooperation of the quinine and the sterically encumbered squaramide moieties catalyzed the Michael...

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Bibliographic Details
Published inAsian journal of organic chemistry Vol. 5; no. 1; pp. 114 - 119
Main Authors Kanberoglu, Esra, Tanyeli, Cihangir
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.01.2016
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
enantioselectivity
Michael addition
organocatalysis
ORGANOCATALYSTS
nitro compounds
asymmetric catalysis
CONJUGATE ADDITION
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Summary: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--nitroalkenes. The cooperation of the quinine and the sterically encumbered squaramide moieties catalyzed the Michael addition reactions at 0 degrees C by using a catalyst loading of only 2mol% 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).
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201500339