395663-83-9Relevant academic research and scientific papers
B(C6F5)3-catalyzed hydrogenation of oxime ethers without cleavage of the N-O bond
Mohr, Jens,Oestreich, Martin
supporting information, p. 13278 - 13281 (2015/01/16)
The hydrogenation of oximes and oxime ethers is usually hampered by N-O bond cleavage, hence affording amines rather than hydroxylamines. The boron Lewis acid B(C6F5)3 is found to catalyze the chemoselective hydrogenation
On the origins of diastereoselectivity in the alkylation of enolates derived from N-1-(1′-Naphthyl)ethyl-O-tert-butylhydroxamates: Chiral Weinreb amide equivalents
Davies, Stephen G.,Goodwin, Christopher J.,Hepworth, David,Roberts, Paul M.,Thomson, James E.
supporting information; experimental part, p. 1214 - 1227 (2010/04/26)
(Chemical Equation Presented) The stereochemical outcome observed upon alkylation of enolates derived from N-1-(1′-naphthyl)ethyl-O-tert- butylhydroxamates (chiral Weinreb amide equivalents) may be rationalized by a chiral relay mechanism. Deprotonation withKHMDS leads to a nonchelated (Z)-enolate inwhich the oxygen atoms adopt an anti-periplanar conformation. The configuration of the N-1-(1′-naphthyl)ethyl group dictates the conformation of the O-tert-butyl group and the configuration adopted by the adjacent pyramidal nitrogen atom. Highly diastereoselective enolate alkylation then proceeds anti to both the bulky tert-butyl group (sterically driven) and the N-lone pair (stereoelectronically driven).
