223505-12-2Relevant academic research and scientific papers
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.
Novel chiral bridged azepanes: Stereoselective ring expansion of 2-azanorbornan-3-yl methanols
Wojaczyńska, Elzbieta,Turowska-Tyrk, Ilona,Skarzewski, Jacek
scheme or table, p. 7848 - 7854 (2012/09/25)
The reaction of 2-azanorbornan-3-yl methanols under Mitsunobu or mesylation conditions with various nucleophiles led to a series of chiral-bridged azepanes with configuration at C-4 dependent on the configuration of the starting alcohol. High yielding, st
An improved synthesis of enantiopure 2-azabicyclo[2.2.1]heptane-3-carboxylic acid
Tararov, Vitali I.,Kadyrov, Renat,Kadyrova, Zenfira,Dubrovina, Natalia,Boerner, Armin
, p. 25 - 28 (2007/10/03)
A facile multigram scale preparation of (1R,3S,4S)-2-azabicyclo[2.2.1]heptane-3-carboxylic acid via stereoselective synthesis of the corresponding α-amino ester hydrochloride is detailed. Hitherto applied protocols for the synthesis of this cyclic proline
Enantioselective Addition of Dialkylzinc Reagents to N-(Diphenylphosphinoyl) Imines Promoted by 2-Azanorbornylmethanols
Guijarro, David,Pinho, Pedro,Andersson, Pher G.
, p. 2530 - 2535 (2007/10/03)
A set of new β-amino alcohols 2, with the 2-azanorbornyl framework, has been prepared and evaluated as promoters for the enantioselective addition of dialkylzinc reagents to N-(diphenylphosphinoyl) imines 1. By variation of the substitution pattern in the ligand, ee's up to 92% could be obtained. Although a stoichiometric amount of the ligand was used, about 90% of it could be recovered during the workup. Amino alcohol 2b, that gave the best enantioselectivities in the stoichiometric reaction, was also applied in a catalytic process, and ee's up to 85% were achieved using 0.25 equiv of the ligand, which is the highest ee obtained so far using that catalytic amount of the ligand. Addition products 3 could be converted into the free amines 4 without racemization by acidic hydrolysis. The utility of ligands 2 as catalysts in the addition of diethylzinc to benzaldehyde has also been investigated, and ee's up to 75% were achieved.
