Squaramide catalyzed alpha-chiral amine synthesis

2018-10-17
Karahan, SEDA
Tanyeli, Cihangir
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.
TETRAHEDRON LETTERS

Suggestions

PFAM catalyzed enantioselective diethylzinc addition to imines
Doğan, Özdemir (2015-01-01)
Chiral amines are important starting materials for the synthesis of biologically important compounds. Enantioselective addition of dialkylzinc reagents to imines is a reliable method for the synthesis of these compounds. Different chiral catalysts were developed and used for this method. Phosphorous based PFAM catalysts were tried for the first time in the enantioselective synthesis of amines by reacting diethylzinc with N-sulfonyl imines and N-diphenylphosphinoyl imines. Chiral amines were isolated with mo...
Enantioselective reduction of ketones with borane catalyzed by cyclic β- amino alcohols prepared from proline
Demir, Ayhan S; Mecitoglu, Idris; Tanyeli, Cihangir; Gülbeyaz, Volkan (Elsevier BV, 1996-12)
New catalysts have been prepared from (S)- and (R)- proline and the asymmetric borane reduction of prochiral ketones using these catalysts has been studied. The secondary alcohols were obtained in 76-95% yield with 57-96% enantiomeric excesses. Copyright (C) 1996 Elsevier Science Ltd
Facile synthesis of (4-nitrophenyl)thio-substituted 1- pyrrolines
Korkmaz, Esra; Zora, Metin; Department of Chemistry (2019)
The importance of heterocyclic compounds is enormous in synthetic organic chemistry due to their presence in bioactive molecules. Five-membered 1-pyrrolines are one of the most important classes of them. They have recently drawn great attention from synthetic chemists since they have a prominent role for the synthesis of a great number of pharmaceutical molecules. Therefore, there is intense research on their synthesis. In this project, we concentrated on the synthesis of (4-nitrophenyl)thio-substituted 1- ...
Resveratrol as a Growth Substrate for Bacteria from the Rhizosphere
Kurt, Zöhre; Spain, Jim C. (2018-05-01)
Resveratrol is among the best-known secondary plant metabolites because of its antioxidant, anti-inflammatory, and anticancer properties. It also is an important allelopathic chemical widely credited with the protection of plants from pathogens. The ecological role of resveratrol in natural habitats is difficult to establish rigorously, because it does not seem to accumulate outside plant tissue. It is likely that bacterial degradation plays a key role in determining the persistence, and thus the ecological...
Enantioselective formal synthesis of pregabalin with bifunctional acid/base organocatalysts
Kapucu, Merve; Tanyeli, Cihangir; Department of Chemistry (2013)
Pregabalin, which is marketed under the brand name of Lyrica by Pfizer, is an important chiral drug in the treatment of epilepsy and neuropathic pain. Since only S-Pregabalin is active for the treatment, asymmetric synthesis was accomplished in 6 steps and the chiral induction was done by transition metal catalysis in industrial production. In this thesis, we applied an alternative synthetic route taken place in 3 steps. The key step comprised the chiral induction done by organocatalysis and the formal asym...
Citation Formats
S. Karahan and C. Tanyeli, “Squaramide catalyzed alpha-chiral amine synthesis,” TETRAHEDRON LETTERS, pp. 3725–3737, 2018, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/48083.