354147-36-7Relevant academic research and scientific papers
Highly diastereoselective aminoalkylation of naphthols with chiral amines mediated by lithium perchlorate solution in diethyl ether
Saidi, Mohammad R.,Azizi, Najmoddin
, p. 389 - 392 (2003)
One-pot, three-component, Mannich reaction of naphthols with in situ prepared imines in 5 M ethereal lithium perchlorate at room temperature affords the corresponding aminoalkylated products in high yields with high diastereoselectivities. The process is exemplified by the reaction of 2-naphthol with (R)-1-phenylethylamine and an aromatic aldehyde in concentrated ethereal lithium perchlorate solution, which affords a highly diastereoselective access to the requisite 2-aminoalkylated product.
Development of chiral heteroleptic magnesium amides; Asymmetric deprotonations mediated by six-membered metallocyclic amidomagnesium naphtholates
Carswell, Emma L.,Kerr, William J.,McArthur, Duncan,Pa?icky, Marek,Watson, Allan J.B.
, p. 7344 - 7349 (2016/01/25)
A series of enantioenriched six-membered metallocyclic amidomagnesium naphtholates were prepared and used to probe the structure-reactivity/selectivity relationships of heteroleptic magnesium base complexes within asymmetric deprotonation reactions. An ef
Solvent-free asymmetric aminoalkylation of electron-rich aromatic compounds: Stereoselective synthesis of aminoalkylnaphthols by crystallization-induced asymmetric transformation
Cimarelli,Mazzanti,Palmieri,Volpini
, p. 4759 - 4765 (2007/10/03)
Electron-rich aromatic compounds such as 2-naphthol give a faster and asymmetric 1-aminoalkylation with high yields when treated with (R)-1-phenylethylamine and aromatic aldehydes in solvent-free conditions. An asymmetric transformation of a second kind, probably induced by the preferential crystallization of one diastereomer, affords the straightforward and stereoselective synthesis of aminoalkylnaphthols. Mechanisms predictable for this asymmetric reaction are reported. The absolute configurations and the conformations of the unknown aminonaphthols are widely ascertained.
