115477-06-0Relevant academic research and scientific papers
Iridium-catalyzed, asymmetric amination of allylic alcohols activated by lewis acids
Yamashita, Yasuhiro,Gopalarathnam, Apsara,Hartwig, John F.
, p. 7508 - 7509 (2007)
The direct, Ir-catalyzed, regio- and enantioselective amination of allylic alcohols with Lewis acid activators to form branched allylic amine products is reported. The reactions of arylamines, benzylic amines, and secondary aliphatic amines in the presence of Nb(OEt)5 as activator occurred with high regioselectivities and high enantioselectivities. These results led to the development of Ir-catalyzed reactions of allylic alcohol with arylamines and BPh3 as activator in catalytic amounts. These reactions are rare examples of enantioselective substitutions of allylic alcohols. They are particularly unusual examples of the substitution of allylic alcohols to generate branched substitution products from monosubstituted allylic alcohols and of enantioselective substitutions of allylic alcohols with amine nucleophiles. Copyright
Counteranion-controlled regioselectivity in palladium-catalyzed allylic amination of dienyl allylic carbonates
Shen, Meng-Lan,Wang, Pu-Sheng,Gong, Liu-Zhu
, (2021/03/01)
A regioselective Pd-catalyzed allylic amination reaction of dienyl allylic carbonates and aromatic amines has been developed by means of phosphoramidite-palladium catalysis. The regioselectivity could be altered by the counterion of the π-allylpalladium intermediate. As a result, either branched Z-dienyl allylic amines or linear conjugated allylic amines were generated in high levels of regioselectivity from the same substrates by tuning the reaction conditions.
Effects of catalyst activation and ligand steric properties on the enantioselective allylation of amines and phenoxides
Leitner, Andreas,Shu, Chutian,Hartwig, John F.
, p. 1093 - 1096 (2007/10/03)
(Chemical Equation Presented) The yields, enantioselectivities, and regioselectivities of the reactions of amines and phenoxides with allylic carbonates in the presence of a metallacyclic iridium catalyst were compared. These data show that both preactiva
A one-pot aza-Wittig based solution and polymer supported route to amines
Hemming,Bevan,Loukou,Patel,Renaudeau
, p. 1565 - 1568 (2007/10/03)
This paper presents a high yielding one-pot solution phase and polymer supported synthesis of a range of primary and secondary amines starting from azides and aldehydes. The synthesis utilises a tandem process which begins with an aza-Wittig reaction between the aldehyde and an iminophosphorane, followed by reduction, or organometallic 1,2-addition reaction, of the resultant imine. The requisite iminophosphoranes were accessed using the highly efficient Staudinger reaction between the azide starting material and a phosphine. The process was applicable to the solid phase by the use of polymer supported iminophosphoranes and polymer supported cyanoborohydride.
Synthesis of Hydroisoindoles via Intramolecular Diels-Alder Reactions of Functionalised Amido Trienes
Mellor, John M.,Wagland, Alison M.
, p. 997 - 1005 (2007/10/02)
Reactions of amino dienes with acryloyl chloride, maleic anhydride, bromomaleic anhydride, and dichloromaleic anhydride were studied.Acylation and intramolecular reaction by Diels-Alder cyclisation gave bicyclic adducts.Adducts of dichloromaleic anhydride
