871563-47-2Relevant academic research and scientific papers
Asymmetric Halocyclizations of 2-Vinylbenzyl Alcohols with Chiral FLPs
Han, Caifang,Feng, Xiangqing,Du, Haifeng
, p. 7325 - 7329 (2021/10/01)
By the use of a chiral frustrated Lewis pair (FLP) consisting of a chiral-diene-derived borane and tBu3P as the catalyst, an asymmetric halocyclization of 2-vinylbenzyl alcohols with NBS or NIS was successfully realized. A variety of optically active 1,3-dihydroisobenofuran derivatives were obtained in high yields with up to 87% ee and could be conveniently converted to other useful chiral compounds.
Rhodium(II)- or Copper(I)-Catalyzed Formal Intramolecular Carbene Insertion into Vinylic C(sp2)?H Bonds: Access to Substituted 1H-Indenes
Zhou, Qi,Li, Shichao,Zhang, Yan,Wang, Jianbo
, p. 16013 - 16017 (2017/11/27)
A rhodium(II)- or copper(I)-catalyzed formal intramolecular carbene insertion into vinylic C(sp2)?H bonds is reported herein. This method provides straightforward access to 1H-indenes with high efficiency and excellent functional-group compatibility. Mechanistically, the reaction is proposed to involve the following sequence: metal carbene formation, intramolecular nucleophilic addition of the double bond to the electron-deficient carbene carbon atom, dearomatization, and finally a 1,5-H shift.
Hydroacylation of 2-vinyl benzaldehyde systems: An efficient method for the synthesis of chiral 3-substituted indanones
Kundu, Kousik,McCullagh, James V.,Morehead Jr., Andrew T.
, p. 16042 - 16043 (2007/10/03)
Asymmetric rhodium-catalyzed hydroacylation has been utilized in the synthesis of 3-substituted indanones with high conversions and enantioselectivity. The hydroacylation reaction of 2-vinyl benzaldehyde had been previously reported to give a low yield of indanone and an unidentified product. We have identified this compound as a dimer of the starting material. Substitution at the α-position of the 2-vinyl benzaldehyde substrates blocks the competitive dimerization reaction and allows the reaction to proceed with yields generally greater than 90%. Utilization of BINAP as a chiral ligand results in good chemical yields and enantioselectivity greater than 95% in most cases. Copyright
