82315-95-5Relevant academic research and scientific papers
The first asymmetric halogen/metal-exchange reaction: Desymmetrization of alcohols with enantiotopic bromoarene substituents
Saelinger, Daniel,Brueckner, Reinhard
experimental part, p. 6688 - 6703 (2010/02/28)
Desymmetrizations of the prochiral bis(bromoaryl)alcohols 1 and 4 were effected by treatment with iPr2Mg and enantiomerically pure lithium alkoxides. The resulting arylmagnesium compounds were quenched with various electrophiles. The absolute and (if relevant) relative configurations of the resulting products were determined. The best ee/yield combination was obtained for the protonolysis furnishing monobromoalcohol (R)-2 (53% ee, 51% yield). The latter was converted into (R)-orphenadrine, an antihistaminic and anticholinergic drug.
Ortho-TMS benzaldehyde: An effective linchpin for type II anion relay chemistry (ARC)
Smith III, Amos B.,Kim, Won-Suk,Wuest, William M.
supporting information; experimental part, p. 7082 - 7086 (2009/04/07)
(Chemical Equation Presented) ARC de triomphe: Ortho-TMS benzaldehyde permits efficient multicomponent union of a variety of nucleophiles and electrophiles, including the first example of a Pd-mediated ARC Type II process. A proof-of-concept synthetic sequence was designed and implemented for construction of a focused library of natural product-like compounds (see scheme). ARC: anion relay chemistry.
Cyclization of o-Allylstyrene via Hydrosilylation: Mechanistic Aspects of Hydrosilylation of Styrenes Catalyzed by Palladium-Phosphine Complexes
Uozumi, Yasuhiro,Tsuji, Hayato,Hayashi, Tamio
, p. 6137 - 6140 (2007/10/03)
Hydrosilylation of o-allylstyrene with trichlorosilane in the presence of 0.3 mol % of a palladium catalyst bearing triphenylphosphine gave trans-1-methyl-2-(trichlorosilylmethyl)indan, l-(2-(2-propenyl)phenyl)-1-trichlorosilylethane, and 1-(2-((E)-1-propenyl)phenyl)-1-trichlorosilylethane. The reaction of styrene with trichlorosilane gave a quantitative yield of 1-phenyl-1-(trichlorosilyl)ethane while allylbenzene did not give silylation products under the same reaction conditions. These results show that the hydropalladation process is operative in the hydrosilylation of styrene derivatives with trichlorosilane catalyzed by palladium-phosphine complexes.
