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


KANBEROĞLU E., TANYELİ C.

ASIAN JOURNAL OF ORGANIC CHEMISTRY, cilt.5, ss.114-119, 2016 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 5 Konu: 1
  • Basım Tarihi: 2016
  • Doi Numarası: 10.1002/ajoc.201500339
  • Dergi Adı: ASIAN JOURNAL OF ORGANIC CHEMISTRY
  • Sayfa Sayıları: ss.114-119

Özet

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).