123535-85-3Relevant articles and documents
Polymer-supported ferrocenyl oxazolines for the catalyzed highly enantioselective phenyl transfer to aldehydes
Bolm, Carsten,Hermanns, Nina,Cla?en, Arno,Muiz, Kilian
, p. 1795 - 1798 (2002)
A new chiral MeO-PEG-supported ferrocenyl oxazoline was synthesized and successfully employed in the enantioselective phenyl transfer to aldehydes. The products were obtained in high yields and with excellent enantioselectivities (up to 97% ee). Furthermo
Boronic acids as versatile aryl sources for the highly enantioselective synthesis of chiral diarylmethanols on multigram scale
Rudolph, Jens,Schmidt, Frank,Bolm, Garsten
, p. 840 - 842 (2005)
Chiral diarylmethanols have been synthesized on gram scale in high yields with excellent enantioselectivities using a catalyst with a ferrocenyl oxazoline-based N,O-ligand and mixtures of diethylzinc and arylboronic acid as an aryl source.
Tropos amino alcohol mediated enantioselective aryl transfer reactions to aromatic aldehydes
Pisani, Laura,Bochicchio, Carmela,Superchi, Stefano,Scafato, Patrizia
, p. 5939 - 5945 (2014)
The preparation of new chiral amino alcohols that possess a flexible biphenylazepine moiety and can work as tropos catalysts, is presented. In these compounds, the sign of the induced axial chirality depends on the nature of stereogenic centers near the flexible fragment and can determine the stereochemical outcome in asymmetric reactions mediated by them. The efficiency of these new ligands has been explored in the asymmetric addition of arylzinc species prepared in situ to aromatic aldehydes. Among them, amino alcohol (1R,2S)-4 gave the best results and afforded optically active diarymethanols, which are precursors of well-known chiral drugs, in high yields and with enantioselectivity up to 96 %.
Nickel-Catalyzed Intermolecular Asymmetric Addition of Aryl Iodides across Aldehydes
Zhu, Ziqi,Xiao, Jieshuai,Li, Mingjie,Shi, Zhuangzhi
supporting information, (2022/02/25)
Enantioenriched alcohols comprise much of the framework of organic molecules. Here, we first report that chiral nickel complexes can catalyze the intermolecular enantioselective addition of aryl iodides across aldehydes to provide diverse optically active secondary alcohols using zinc metal as the reducing agent. This method shows a broad substrate scope under mild reaction conditions and precludes the traditional strategy through the pre-generation of organometallic reagents. Mechanistic studies indicate that an in situ formed arylnickel, instead of an arylzinc, adds efficiently to aldehydes, forming a new C?C bond and a chiral nickel alkoxide that may be turned over by zinc powder.
Binaphthyl-prolinol chiral ligands: Design and their application in enantioselective arylation of aromatic aldehydes
Yao, Chao,Chen, Yaoqi,Sun, Ruize,Wang, Chao,Huang, Yue,Li, Lin,Li, Yue-Ming
supporting information, p. 3644 - 3655 (2021/05/04)
Binaphthyl-prolinol ligands were designed and applied in enantioselective arylation of aromatic aldehydes and sequential arylation-lactonization of methyl 2-formylbenzoate. Under optimized conditions, the reactions provided the desired diarylmethanols and 3-aryl phthalides in up to 96% yields with up to 99% ee and up to 89% yields with up to 99% ee, respectively. In particular, essentially optically pure 3-aryl phthalides (over 99% ee) were obtained in large quantities through recrystallization. This journal is
