204851-80-9Relevant articles and documents
Copper-Catalyzed Synthesis of γ-Amino Acids Featuring Quaternary Stereocenters
Gómez, José Enrique,Guo, Wusheng,Gaspa, Silvia,Kleij, Arjan W.
supporting information, p. 15035 - 15038 (2017/11/20)
The first general asymmetric synthesis of γ,γ-disubstituted γ-amino acids by copper-catalyzed ring opening of nonstrained lactones with amines is reported. This approach features ample scope, operational simplicity, and wide functional-group diversity. The catalytic process allows access to a series of highly functionalized enantioenriched γ-amino acids featuring quaternary stereocenters with excellent enantiomeric ratios of up to 98:2 and excellent yields of up to 98 %.
Second-generation DBFOX ligands for the synthesis of β-substituted α-amino acids via enantioselective radical conjugate additions
Banerjee, Biplab,Capps, Steven G.,Kang, Junghoon,Robinson, Joshua W.,Castle, Steven L.
experimental part, p. 8973 - 8978 (2009/04/11)
(Chemical Equation Presented) A set of second-generation DBFOX ligands possessing extended aryl or benzyl-type groups was synthesized. The requisite amino alcohols were either commercially available (DBFOX/Bn) or constructed via Sharpless asymmetric amino
An effective and useful synthesis of enantiomerically enriched arylglycinols
Bandini, Marco,Cozzi, Pier Giorgio,Gazzano, Massimo,Umani-Ronchi, Achille
, p. 1937 - 1942 (2007/10/03)
A two-step synthesis of racemic arylglycinols, together with a simple and straightforward methodology for their resolution, is described. This method constitutes a practical means of preparing racemic and optically pure electron-rich or electron-poor subs
4-naphthyl-substituted Bis(oxazoline): A new, easily recoverable and efficient chiral ligand in asymmetric catalysis of the diels-alder reaction
Crosignani, Stefano,Desimoni, Giovanni,Faita, Giuseppe,Righetti, PierPaolo
, p. 15721 - 15730 (2007/10/03)
2,2-Bis{2-[(4R)-(2'-naphthyl)-1,3-oxazolinyl]}propane and its (45) enantiomer were prepared starting from 2-vinylnaphthalene, following the Sharpless protocol, and were found to be optically pure (ee ≥99.5%) by hplc analysis. These new bis(oxazolines) are efficient chiral ligands in the asymmetric catalysis of the Dieis-Alder reaction of Nalkenoyl-oxazolidin-2- one derivatives since endo cycloadducts are obtained with up to 94% ee. Different Lewis acids were tested, the best one being the Mg(II) cation derived from the corresponding triflate. A remarkable feature of such new chiral ligands is the low solubility in polar solvents, so that the chiral ligand can be easily recovered by a simple filtration. The recovered ligand can be directly reused in other asymmetric syntheses, without any further purification and, overall, without any drop in the induced enantioselectivities.
