215674-17-2Relevant academic research and scientific papers
Application of polyamines and amino acid derivatives based on 2-azabicycloalkane backbone in enantioselective aldol reaction
Iwan, Dominika,Kamińska, Karolina,Wojaczyńska, El?bieta
, (2021/09/04)
Carbon–carbon bond forming reactions, such as aldol reaction and condensation, belong to extremely desired transformations as manifested by >25,000 entries in SciFinder. Their stereoselective variant requires the use of an appropriate catalyst with a stri
Synthesis and cytotoxic activity of chiral sulfonamides based on the 2-azabicycloalkane skeleton
Iwan, Dominika,Kamińska, Karolina,Kochel, Andrzej,Madlener, Sibylle,Pinter, Matthias,Rohr-Udilova, Nataliya,Samadaei, Mahzeiar,Senfter, Daniel,Wojaczyńska, Elzbieta,Wojaczyński, Jacek
, (2020/05/29)
A series of chiral sulfonamides containing the 2-azabicycloalkane scaffold were prepared from aza-Diels–Alder cycloadducts through their conversion to amines based on 2-azanorbornane or the bridged azepane skeleton, followed by the reaction with sulfonyl chlorides. The cytotoxic activity of the obtained bicyclic derivatives was evaluated using human hepatocellular carcinoma (HCC), medulloblastoma (MB), and glioblastoma (GBM) cell lines. Chosen compounds were shown to notably reduce cell viability as compared to nonmalignant cells.
2-Azanorbornane-Based Amino Alcohol Organocatalysts for Asymmetric Michael Reaction of β-Keto Esters with Nitroolefins
Togashi, Rei,Chennapuram, Madhu,Seki, Chigusa,Okuyama, Yuko,Kwon, Eunsang,Uwai, Koji,Tokiwa, Michio,Takeshita, Mitsuhiro,Nakano, Hiroto
, p. 3882 - 3889 (2019/06/21)
New optically active 2-azanorbornane-based amino alcohol organocatalysts were designed and synthesized, and these catalysts were successfully employed in the asymmetric Michael reaction of β-keto esters with nitroolefins to obtain the corresponding chiral
Synthesis, structure and antiproliferative activity of chiral polyamines based on a 2-azanorbornane skeleton
Kamińska, Karolina,Wojaczyńska, El?bieta,Wietrzyk, Joanna,Turlej, Eliza,B?a?ejczyk, Agnieszka,Wieczorek, Robert
, p. 753 - 758 (2016/07/29)
A series of enantiopure 2-azanorbornane-based amines were prepared via a stereoselective aza-Diels–Alder reaction and further modifications of the obtained cycloadduct. In particular, derivatives containing two bicyclic moieties linked by [Formula presented] fragments were synthesized. Two dimeric derivatives exhibited a significant antiproliferative activity against selected cell lines, comparable to cisplatin in certain cases.
Zinc complexes formed by 2,2′-bipyridine and 1,10-phenanthroline moieties combined with 2-azanorbornane: Modular chiral catalysts for aldol reactions
Wojaczyńska, El?bieta,Skar?ewski, Jacek,Sidorowicz, ?ukasz,Wieczorek, Robert,Wojaczyński, Jacek
, p. 9795 - 9805 (2016/11/11)
Chiral scaffolds of 2-azabicyclo[2.2.1]heptane and 2-azabicyclo[3.2.1]octane were used for the construction of new modular catalysts containing complexing moieties pyridine, 2,2′-bipyridine and 1,10-phenanthroline appended by an imine linkage. The coordin
Chelating 2-azanorbornyl derivatives as effective nitrogen-nitrogen and nitrogen-chalcogen donating ligands in palladium-catalyzed asymmetric allylic alkylation
Wojaczynska, Elzbieta,Skarzewski, Jacek
scheme or table, p. 2252 - 2257 (2009/04/04)
New chiral 2-azanorbornane derivatives were prepared and used as (N,S)-, (N,Se)-, and (N,N)-donating ligands in a palladium-catalyzed asymmetric allylic alkylation, giving up to 95% ee and 92% yield.
A short, convenient synthesis of enantiomerically pure N-protected 2-azanorbornane-3-carboxaldehydes and related amino alcohols
Genov, Miroslav,Scherer, Gerd,Studer, Martin,Pfaltz, Andreas
, p. 2037 - 2042 (2007/10/03)
The aza-Diels-Alder reaction between cyclopentadiene and the bis(1-phenylethyl)imine of glyoxal provides a short route to the two enantiomerically pure exo-diastereomers of N-(1-phenylethyl)-2-azanorbornane-3-carboxaldehyde. Addition of 1-naphthylmagnesiu
Allylic alcohols via catalytic asymmetric epoxide rearrangement
Soedergren, Mikael J.,Bertilsson, Sophie K.,Andersson, Pher G.
, p. 6610 - 6618 (2007/10/03)
Epoxides using chiral lithium amides, but other than for a small subset of meso-epoxides, insufficient reactivity and enantioselectivity hamper the existing methods. Furthermore, the chiral reagents are often required in large excess. This study presents a general and highly enantioselective process that, in addition, is based on catalytic amounts (5 mol %) of enantiopure (1S,3R,4R)-3-(1-pyrrolidinyl)methyl-2-azabicyclo[2.2.1]heptane and lithium diisopropylamide as the stoichiometric base. The influence of structural modification of the catalyst is studied in terms of activity, enantioselectivity, and aggregation behavior. The utility of the process is demonstrated by its application to a variety of epoxide derivatives (≥94% ee for 11 out of 14 examples), including the formal syntheses of, e.g., a prostaglandin core unit, epibatidine, carbovir, faranal, and lasiol. The system is readily extended to the resolution of racemic epoxides, which allows access to highly enantioenriched epoxides or allylic alcohols, even at conversions near 50%.
A theoretical and experimental study of the asymmetric addition of dialkylzinc to N-(diphenylphosphinoyl)benzalimine
Brandt, Peter,Hedberg, Christian,Lawonn, Klaus,Pinho, Pedro,Andersson, Pher G.
, p. 1692 - 1699 (2007/10/03)
The mechanism of the enantioselective addition of diethylzinc to N-(diphenylphosphinoyl)benzalimine with catalysis by bicyclic 2-azanorbornyl-3-methanols was studied by quantum chemical calculations. The mechanism proved to differ from that of the addition of diethylzinc to aldehydes and also from an earlier proposed mechanism. The results of the calculations were used to identify several factors responsible for the selectivity. The theoretical evaluation was performed in connection with an experimental study of the effects of introducing an additional stereocenter in the ligand. An efficient route to both diastereomers of new bicyclic 2-azanorbornyl-3-methanols with an additional chiral center (the secondary alcohol group) is also presented. In the best case, an enantiomeric excess of up to 97% was obtained with these new ligands.
