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, sa.1, ss.114-119, 2016 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 5 Sayı: 1
  • Basım Tarihi: 2016
  • Doi Numarası: 10.1002/ajoc.201500339
  • Dergi Adı: ASIAN JOURNAL OF ORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
  • Sayfa Sayıları: ss.114-119
  • Anahtar Kelimeler: asymmetric catalysis, enantioselectivity, Michael addition, nitro compounds, organocatalysis, CONJUGATE ADDITION, ORGANOCATALYSTS
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

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).