24066-86-2Relevant articles and documents
Iron-Catalyzed Highly Enantioselective Hydrogenation of Alkenes
Lu, Dongpo,Lu, Peng,Lu, Zhan,Ren, Xiang,Sun, Yufeng,Xu, Haofeng
supporting information, p. 12433 - 12438 (2021/08/23)
Here, we reported for the first time an iron-catalyzed highly enantioselective hydrogenation of minimally functionalized 1,1-disubstituted alkenes to access chiral alkanes with full conversion and excellent ee. A novel chiral 8-oxazoline iminoquinoline ligand and its iron complex have been designed and synthesized. This protocol is operationally simple by using 1 atm of hydrogen gas and shows good functional group tolerance. A primary mechanism has been proposed by the deuterium-labeling experiments.
Tunable phosphoramidite ligands for asymmetric hydrovinylation: Ligands par excellence for generation of all-carbon quaternary centers
Smith, Craig R.,Hwan, Jung Lim,Zhang, Aibin,RajanBabu
experimental part, p. 2089 - 2100 (2010/02/28)
α-Alkylstyrenes undergo efficient hydrovinylation (addition of ethene) in the presence of a nickel catalyst prepared from [(allyl)NiBr] 2, Na+[BAr4]- [Ar = 3,5-bis(trifluoromethyl)phenyl], and a phosphoramidite ligand giving products in excellent yields and enantioselectivities. In many cases phosphoramidites derived from achiral 2,2′-biphenol are almost as good as ligands derived from the more expensive enantiopure 1,1′-bi(2-naphthol)s. The hydrovinylation products, which carry two versatile latent functionalities, an aryl and a vinyl group, are potentially useful for the synthesis of several important natural products containing benzylic all-carbon quaternary centers. Georg Thieme Verlag Stuttgart.
Novel nickel-catalyzed coupling reaction of allyl ethers with chlorosilanes, alkyl tosylates, or alkyl halides promoted by vinyl-Grignard reagent leading to allylsilanes or alkenes
Terao, Jun,Watabe, Hiroyasu,Watanabe, Hiroyuki,Kambe, Nobuaki
, p. 1674 - 1678 (2007/10/03)
A new method for a carbon-silicon or carbon-carbon bond forming reaction between allyl ethers and chlorosilanes, alkyl tosylates, or alkyl halides giving rise to allylsilanes or alkenes has been developed. This reaction proceeds efficiently at ambient temperature by the combined use of nickel catalysts and a vinyl-Grignard reagent. A possible reaction pathway involving the formation of allyl-Grignard reagents via transmetallation of π-allylnickel complexes with the vinyl-Grignard reagent and subsequent trapping of the thus formed allyl-Grignard reagents with electrophiles is proposed.
