789448-73-3Relevant academic research and scientific papers
Ir-catalyzed allylic amination/ring-closing metathesis: A new route to enantioselective synthesis of cyclic β-amino alcohol derivatives
Jun, Hee Lee,Shin, Seunghoon,Kang, Jahyo,Lee, Sang-Gi
, p. 7443 - 7446 (2007)
(Chemical Equation Presented) Ir-catalyzed allylic aminations of (E)-4-benzyloxy-2-butenyl methyl carbonate with benzylamine using Feringa's (Sa,Sc,Sc)- phosphoramidite as a chiral ligand afforded linear-aminated achiral p
Palladium-catalyzed vicinal amino alcohols synthesis from allyl amines by in situ tether formation and carboetherification
Orcel, Ugo,Waser, Jerome
supporting information, p. 5250 - 5254 (2015/04/27)
Vicinal amino alcohols are important structural motifs of bioactive compounds. Reported herein is an efficient method for their synthesis based on the palladium-catalyzed oxy-alkynylation, oxy-arylation, or oxy-vinylation of allylic amines. High regio- and stereoselectivity were ensured through the in situ formation of a hemiaminal tether using the cheap commercially available trifluoroacetaldehyde in its hemiacetal form. The obtained compounds are important building blocks, which can be orthogonally deprotected to give either free alcohols, amines, or terminal alkynes.
Stereoselective synthesis of imidazolidin-2-ones via Pd-catalyzed alkene carboamination. Scope and limitations
Fritz, Jonathan A.,Wolfe, John P.
, p. 6838 - 6852 (2008/09/21)
A method for the synthesis of imidazolidin-2-ones from N-allylureas and aryl or alkenyl bromides via Pd-catalyzed carboamination reactions is described. The N-allylurea precursors are prepared in one step from readily available allylic amines and isocyanates, and the Pd-catalyzed reactions effect the formation of a C-C bond, a C-N bond, and up to two stereocenters in a single step. Good diastereoselectivities are obtained for the conversion of substrates bearing allylic substituents to 4,5-disubstituted imidazolidin-2-ones, and excellent selectivity for the generation of products resulting from syn-addition across the alkene is observed when substrates derived from cyclic alkenes or E-1,2-disubstituted alkenes are employed. A brief discussion of reaction mechanism and product stereochemistry is presented.
