Squaramide catalyzed alpha-chiral amine synthesis

Karahan S., TANYELİ C.

TETRAHEDRON LETTERS, vol.59, no.42, pp.3725-3737, 2018 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 59 Issue: 42
  • Publication Date: 2018
  • Doi Number: 10.1016/j.tetlet.2018.08.034
  • Journal Name: TETRAHEDRON LETTERS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.3725-3737
  • Keywords: 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
  • Middle East Technical University Affiliated: Yes

Abstract

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.