952744-50-2Relevant academic research and scientific papers
Rhodium-Catalyzed Enantioselective Hydroamination of Alkynes with Indolines
Chen, Qing-An,Chen, Zhiwei,Dong, Vy M.
, p. 8392 - 8395 (2015)
The hydroamination of internal alkynes via tandem rhodium catalysis gives branched N-allylic indolines with high regio- and enantioselectivity. An acid switch provides access to the linear isomer in preference to the branched isomer by an isomerization me
Time-dependent enantiodivergent synthesis via sequential kinetic resolution
Tu, Hang-Fei,Yang, Pusu,Lin, Zi-Hua,Zheng, Chao,You, Shu-Li
, p. 838 - 844 (2020/07/03)
The preparation of both enantiomers of chiral molecules is among the most fundamental tasks in organic synthesis, medicinal chemistry and materials science. Achieving this goal typically requires reversing the absolute configuration of the chiral component employed in the reaction system that is being used. The task becomes challenging when the natural source of the chiral component is not available in both configurations. Herein, we report a time-dependent enantiodivergent synthesis, in which an Ir-catalysed allylic substitution reaction uses one catalyst sequentially to promote two kinetic resolution reactions, enabling the synthesis of both enantiomers of the product using the same enantiomer of a chiral catalyst. The appropriate permutation of individual reaction rates is essential for the isolation of the chiral products in opposite configurations with high enantiopurity when quenched at different reaction times. This work provides an alternative solution for the preparation of both enantiomers of chiral molecules. [Figure not available: see fulltext.].
Iridium-catalyzed allylic substitutions with cyclometalated phosphoramidite complexes bearing a dibenzocyclooctatetraene ligand: Preparation of (π-Allyl)Ir complexes and computational and NMR spectroscopic studies
Raskatov, Jevgenij A.,Jaekel, Mascha,Straub, Bernd F.,Rominger, Frank,Helmchen, Guenter
, p. 14314 - 14328 (2013/01/15)
(π-Allyl)Ir complexes derived from dibenzocyclooctatetraene and phosphoramidites by cyclometalation are effective catalysts for allylic substitution reactions of linear monosubstituted allylic carbonates. These catalysts provide exceptionally high degrees
Iridium-catalyzed asymmetric allylic amination with polar amines: Access to building blocks with lead-like molecular properties
Tosatti, Paolo,Horn, Joachim,Campbell, Amanda J.,House, David,Nelson, Adam,Marsden, Stephen P.
, p. 3153 - 3157 (2011/03/18)
The combination of an air-stable iridium catalyst and the dipolar aprotic solvent dimethyl sulfoxide (DMSO) allowed, for the first time, the systematic exploitation of highly polar, functionalized amines in asymmetric allylic substitutions: low molecular
Iridium-catalyzed, asymmetric amination of allylic alcohols activated by lewis acids
Yamashita, Yasuhiro,Gopalarathnam, Apsara,Hartwig, John F.
, p. 7508 - 7509 (2008/02/11)
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
Sequential catalytic isomerization and allylic substitution. Conversion of racemic branched allylic carbonates to enantioenriched allylic substitution products
Shekhar, Shashank,Trantow, Brian,Leitner, Andreas,Hartwig, John F.
, p. 11770 - 11771 (2007/10/03)
A catalytic protocol for the conversion of readily accessible racemic, branched aromatic allylic esters to branched allylic amines, ethers, and alkyls has been developed. Palladium-catalyzed isomerization of branched allylic esters to terminal allylic esters, followed by sequential iridium-catalyzed allylic substitution, gave the branched allylic products in good yield with high regioisomeric and enantiomeric selectivity. Both electron-rich and electron-poor branched allylic esters gave products in >90% ee. High enantiomeric excesses were also observed for the products from the reactions of 2-thienyl acetates and dienyl carbonates. Copyright
