1133733-49-9Relevant academic research and scientific papers
Structure–enantioselectivity correlation in NHC–Au(I) catalysis for 1,6-enynecyclizations
Gung, Benjamin W.,Holmes, Michael R.,Jones, Caleb A.,Ma, Ruoyu,Barnes, Charles L.
, p. 3912 - 3915 (2016)
A direct correlation of the NHC ligand structure and the induced enantioselectivity has been uncovered for a series of new chiral gold(I) complexes. The Au(I)Cl complexes were identified by1H,13C NMR spectroscopy, and X-ray structure analysis. The corresponding activated Au(I) catalysts with a phenyl nitrile dynamic ligand are prepared and used in the catalysis of 1,6-enyne cyclization reactions. High chemical yields and good enantioselectivity have been obtained with 6%?mol of the chiral NHC–Au(I) catalysts. The products in these reactions reach up to 75% ee. The structure of the chiral NHC ligand, where an ortho-biphenyl moiety is connected to the nitrogen atoms, the 3,5-dialkyl distal phenyl group plays a determining role in enantioselectivity.
Chiral carbene approach to gold-catalyzed asymmetric cyclization of 1,6-enynes
Matsumoto, Yasumasa,Selim, Khalid B.,Nakanishi, Hirotsugu,Yamada, Ken-ichi,Yamamoto, Yasutomo,Tomioka, Kiyoshi
, p. 404 - 406 (2010)
Chiral C2-symmetric N-heterocyclic carbenes (NHCs) were tested for their stereocontrolling abilities in gold(I)-catalyzed asymmetric cyclization of 1,6-enynes giving the corresponding cyclopentane derivatives with moderate enantioselectivity of
Steric tuning of C2-symmetric chiral N-heterocyclic carbene in gold-catalyzed asymmetric cyclization of 1,6-enynes
Yamada, Ken-Ichi,Matsumoto, Yasumasa,Selim, Khalid B.,Yamamoto, Yasutomo,Tomioka, Kiyoshi
scheme or table, p. 4159 - 4165 (2012/07/27)
Steric tuning of C2-symmetric chiral N-heterocyclic carbene (NHC) was performed in Au(I)-catalyzed asymmetric cyclization of 1,6-enyne. Higher enantioselectivity was realized when chiral NHC-AuCl/AgSbF6 catalysts whose N-substituent on the NHC overlays the Au-Cl bond was utilized.
Towards asymmetric Au-catalyzed hydroxy- and alkoxycyclization of 1,6-enynes
Chao, Chung-Meng,Genin, Emilie,Toullec, Patrick Y.,Genêt, Jean-Pierre,Michelet, Véronique
experimental part, p. 538 - 545 (2009/06/05)
The efficiency of a Au(III)/chiral ligand system has been studied. The association of several chiral mono- and bidentate phosphanes with gold has been tested in the formal addition of an oxygen nucleophile to an alkene followed by a cyclization process, n
