351536-34-0Relevant academic research and scientific papers
Highly enantioselective synthesis of α-trichloromethyldihydropyrans catalyzed by bifunctional organocatalysts
Wang, Hai-Feng,Li, Peng,Cui, Hai-Feng,Wang, Xiao-Wei,Zhang, Jun-Kang,Liu, Wen,Zhao, Gang
supporting information; experimental part, p. 1774 - 1780 (2011/04/15)
The enantioselective Michael addition of α-cyanoketones to α,β-unsaturated trichloromethyl ketones was firstly reported. With a phenylalanine-derived bifunctional piperazine/thiourea catalyst, a series of α-trichloromethyldihydropyrans were obtained with
Kinetic resolution of acyclic secondary allylic silyl ethers catalyzed by chiral ketones
Yang,Jiao,Yip,Lai,Wong
, p. 4619 - 4624 (2007/10/03)
Kinetic resolution of acyclic secondary allylic silyl ethers by chiral dioxiranes generated in situ from chiral ketones (R)-1 and (R)-2 and Oxone was investigated. An efficient and catalytic method has been developed for kinetic resolution of those substrates with a CCl3, tert-butyl, or CF3 group at the α-position. In particular, high selectivities (S up to 100) were observed for kinetic resolutions of racemic α-trichloromethyl allylic silyl ethers 7 and 9-15 catalyzed by ketones (R)-2. Both the recovered substrates and the resulting epoxides were obtained in high enantiomeric excess. On the basis of steric and electrostatic interactions between the chiral dioxiranes and the racemic substrates, a model was proposed to rationalize the enantioselectivities and diastereoselectivities in the chiral ketone-catalyzed kinetic resolution process.
