Squaramide catalyzed alpha-chiral amine synthesis

Karahan S., TANYELİ C.

TETRAHEDRON LETTERS, cilt.59, sa.42, ss.3725-3737, 2018 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 59 Sayı: 42
  • Basım Tarihi: 2018
  • Doi Numarası: 10.1016/j.tetlet.2018.08.034
  • Dergi Adı: TETRAHEDRON LETTERS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.3725-3737
  • Anahtar Kelimeler: Squaramide, alpha-Chiral amine, Asymmetric organocatalysis, Bifunctional organocatalyst, AZA-MICHAEL/MICHAEL ADDITION, ENANTIOSELECTIVE MICHAEL ADDITION, ORGANOCATALYTIC ASYMMETRIC-SYNTHESIS, HENRY REACTION, MANNICH REACTION, VINYLOGOUS MANNICH, DERIVATIVES, NITROALKANES, CONSTRUCTION, IMINES
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

Enantiomerically pure alpha-chiral amines, have been commonly utilized as resolving agents and chiral auxiliaries and are currently found in 40% of active pharmaceutical ingredients. Hence, development of highly stereoselective metal-free protocols regarding atom-economy and large-scale applications becomes a major issue. In this respect, chiral bifunctional H-bonding squaramides have been successfully applied for both amine synthesis and functionalization of amines in the last decade. This survey summarizes asymmetric synthesis of chiral amines by various carbon-carbon and carbon-nitrogen bond formation with squaramide catalysis as a particular focus of interest. (C) 2018 Published by Elsevier Ltd.