36851-76-0Relevant academic research and scientific papers
Regioselective Ylide Formation on Acetal-Functionalized Trialkyl Phosphonium Salts: Extending the Scope of Carbonyl Homologation
Narayanappa, Arkesh,Hurem, David,McNulty, James
supporting information, p. 2961 - 2965 (2017/10/06)
The discovery of a complex-induced proximity effect and scope of regioselective ylide formation on acetal- and ketal-functionalized trialkylphosphine-derived phosphonium salts is explored as a route to homologated unsaturated carbonyl derivatives.
Iron catalyzed methylation and ethylation of vinyl arenes
Zhu, Nengbo,Zhao, Jianguo,Bao, Hongli
, p. 2081 - 2085 (2017/03/09)
Short alkyl chain Heck (type) reactions, especially methyl Heck reactions, are a difficult aspect of the alkyl Heck reaction. To provide a solution to this problem, iron-catalyzed methyl, ethyl and propyl Heck reactions were developed using readily available alkyl peroxides as alkyl sources. The reaction conditions were mild, clean, and easy to handle. No additive was needed, and no hazardous waste was generated. The products were obtained in up to 99% yield of one isomer for most situations. This reaction works for many types of olefin and tolerates a variety of functional groups. Several late-stage functionalizations of natural products and drug molecules were conducted to demonstrate the synthetic applications of this reaction.
Catalytic asymmetric carbong-carbon bond formation via allylic alkylations with organolithium compounds
Perez, Manuel,Fananas-Mastral, Martin,Bos, Pieter H.,Rudolph, Alena,Harutyunyan, Syuzanna R.,Feringa, Ben L.
experimental part, p. 377 - 381 (2012/01/06)
Carbon-carbon bond formation is the basis for the biogenesis of nature's essential molecules. Consequently, it lies at the heart of the chemical sciences. Chiral catalysts have been developed for asymmetric C-C bond formation to yield single enantiomers from several organometallic reagents. Remarkably, for extremely reactive organolithium compounds, which are among the most broadly used reagents in chemical synthesis, a general catalytic methodology for enantioselective C-C formation has proven elusive, until now. Here, we report a copper-based chiral catalytic system that allows carbon-carbon bond formation via allylic alkylation with alkyllithium reagents, with extremely high enantioselectivities and able to tolerate several functional groups. We have found that both the solvent used and the structure of the active chiral catalyst are the most critical factors in achieving successful asymmetric catalysis with alkyllithium reagents. The active form of the chiral catalyst has been identified through spectroscopic studies as a diphosphine copper monoalkyl species.
