30235-98-4Relevant articles and documents
Ruthenium-catalyzed coupling of α-carbonyl phosphoniums with sulfoxonium ylidesviaC-H activation/Wittig reaction sequences
Chen, Tian,Ding, Zhiqiang,Guan, Yuqiu,Zhang, Ruike,Yao, Jinzhong,Chen, Zhangpei
supporting information, p. 2665 - 2668 (2021/03/16)
A Ru(ii)-catalyzed coupling of various α-carbonyl phosphoniums with sulfoxonium ylides has been realized for the facile synthesis of 1-naphthols in good to excellent yields. This oxidant-free transformation proceeds through Ru-catalyzed C-H activation of phosphoniums, Ru-carbene insertion, and intramolecular Wittig reaction processes.
Catalytic Asymmetric Aziridination of Benzhydryl Imines and Diazoacetate Esters with BOROX Catalysts from 3,3′-Disubstituted VANOL Ligands
Guan, Yong,Lu, Zhenjie,Mohammadlou, Aliakbar,Staples, Richard J.,Wulff, William D.,Yin, Xiaopeng
, p. 2073 - 2091 (2020/08/17)
This work details the synthesis of 22 new chiral VANOL ligands that differ by the nature of the substituent in the 3- and 3′-positions of the ligand. These ligands were incorporated into boroxinate catalysts that were used to screen the catalytic asymmetric aziridination of benzhydryl imines with ethyl diazoacetate. Each catalyst was screened in the reaction of imines generated from benzaldehyde and cyclohexanecarboxaldehyde and some with 4-nitro- and 4-methoxybenzaldehyde. In addition, the first report of the effect of the ester substituent of the diazoacetate ester on the asymmetric induction in these aziridination reactions is presented. The first X-ray structure of a boroxinate catalyst generated from a VANOL-derived ligand is also reported.
A succinct synthesis of the vaulted biaryl ligand vanol via a dienone-phenol rearrangement
Ding, Zhensheng,Xue, Song,Wulff, William D.
, p. 2130 - 2146 (2011/10/18)
Vanol is a member of the vaulted biaryl family of ligands and it has been proven to be very effective in a number of asymmetric catalytic reactions. The previous synthesis of vanol, while effective, is limited by the cost of reagents involved. The present work evaluates three different approaches to the synthesis of 3-phenyl-1-naphthol, a key intermediate in the synthesis of vanol. The first approach has its key step as the Michael addition of a benzyl Grignard to methyl cinnamate. In the second approach the key step is the first step, a Reformatsky reaction of ethyl bromoacetate and deoxybenzoin. The final and most-efficient approach involves a dienone-phenol rearrangement of a 4-aryl-1-tetralenone generated in-situ from the reaction of 4-chloro-1-naphthol with AlCl3 and benzene, and preliminary results are reported on the extension of this method to substituted vanol derivatives.
