960409-35-2Relevant academic research and scientific papers
Asymmetric intramolecular hydroamination of allenes using mononuclear gold catalysts
Michon, Christophe,Medina, Florian,Abadie, Marc-Antoine,Agbossou-Niedercorn, Francine
, p. 5589 - 5600 (2013/11/06)
The intramolecular gold-catalyzed asymmetric hydroamination of allenes was studied by screening a series of mononuclear gold(I) and -(III) complexes in combination with silver salts. Among the various chiral monophosphine and diaminocarbene ligands tried,
Silver-catalysed enantioselective addition of O-H and N-H bonds to allenes: A new model for stereoselectivity based on noncovalent interactions
Arbour, Jannine L.,Rzepa, Henry S.,Adrio, Luis A.,Barreiro, Elena M.,Hii, King Kuok,Contreras-Garcia, Julia
, p. 11317 - 11324,8 (2020/08/31)
The ability of silver complexes to catalyse the enantioselective addition of O-H and N-H bonds to allenes is demonstrated for the first time by using optically active anionic ligands that were derived from oxophosphorus(V) acids as the sources of chiralit
Gold(I)-catalyzed enantioselective intramolecular dehydrative amination of allylic alcohols with carbamates
Mukherjee, Paramita,Widenhoefer, Ross A.
supporting information; experimental part, p. 1405 - 1407 (2012/03/11)
Aliphatic nitrogen heterocycles either five- or six-membered are formed in high yield and with up to 94 %ee when a 1:2 mixture of [(S)-2](AuCl)2 and AgClO4 is used as the catalyst for the title reaction. Copyright
Gold(I)-catalyzed dynamic kinetic enantioselective intramolecular hydroamination of allenes
Zhang, Zhibin,Bender, Christopher F.,Widenhoefer, Ross A.
, p. 14148 - 14149 (2008/09/18)
Treatment of benzyl 6-methyl-2,2-diphenyl-4,5-octadienyl carbamate (2a) with a catalytic 1:2 mixture of [(S)-3,5-t-Bu-4-MeO-MeOBIPHEP]Au2Cl2 [(S)-1] and AgClO4 (5 mol %) led to isolation of a 3.1:1 mixture of (R,Z)-3a and (R,E)-3a in 94% combined yield with 96 and 76% ee, respectively. Analyses of concentration versus time and/or conversion plots for the reaction of both racemic and enantiomerically enriched 2a with 1 were consistent with conversion of (R)-2a to (R,Z)-3a in the matched reaction manifold and conversion of (S)-2a to (R,E)-3a in the mismatched reaction manifold via the net anti-addition of Au and N across the internal C=C bond of 2a. Copyright
Gold(I)-catalyzed enantioselective hydroamination of N-allenyl carbamates
Zhang, Zhibin,Bender, Christopher F.,Widenhoefer, Ross A.
, p. 2887 - 2889 (2008/02/08)
Treatment of the W-4,5-hexadienyl carbamate 2a with a catalytic 1:2 mixture of [(S)-1]Au2Cl2 [(S)-1 = (S)-3,5-t-Bu-4-MeO-MeOBIPHEP] and AgClO4 in m-xylene at -40°C for 24 h led to isolation of 2-vinylpyrrolidine 3a in 97% yield with 81% ee. Gold(I)-catalyzed enantioselective hydroamination was effective for a number of carbamate groups and tolerated terminal disubstitutution of the allenyl moiety.
