Enantioselective sulfa-Michael addition reaction of methyl thioglycolate to chalcones derivatives with sterically encumbered quinine squaramide organocatalyst

HASILCIOĞULLARI D., TANYELİ C.

TETRAHEDRON LETTERS, cilt.59, sa.14, ss.1414-1416, 2018 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 59 Sayı: 14
  • Basım Tarihi: 2018
  • Doi Numarası: 10.1016/j.tetlet.2018.02.068
  • Dergi Adı: TETRAHEDRON LETTERS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1414-1416
  • Anahtar Kelimeler: Asymmetric catalysis, Asymmetric synthesis, Organocatalysis, Conjugate addition, Sulfa-Michael addition, CHIRAL PRIMARY AMINE, CONJUGATE ADDITION, BIFUNCTIONAL ORGANOCATALYSTS, ASYMMETRIC ORGANOCATALYSIS, CATALYST, KETONES, NITROALKENES, ACCESS, THIOLS
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

Asymmetric organocatalytic sulfa-Michael reactions give access to enantiomerically enriched sulfur containing adducts that can be used as valuable chiral building blocks. A variety of chalcone derivatives were allowed to react with methyl thioglycolate under optimized conditions, in the presence of a bifunctional quinine derived sterically encumbered squaramide organocatalyst, giving rise to excellent stereoselectivities, up to 99% ee. The designed catalyst system proved to be efficient even at gram scale and under milder reaction conditions. (C) 2018 Elsevier Ltd. All rights reserved.