ASIAN JOURNAL OF ORGANIC CHEMISTRY, vol.5, no.1, pp.114-119, 2016 (SCI-Expanded)
Article / Article
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
asymmetric catalysis, enantioselectivity, Michael addition, nitro compounds, organocatalysis, CONJUGATE ADDITION, ORGANOCATALYSTS
Middle East Technical University Affiliated:
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).