83945-70-4Relevant academic research and scientific papers
High performance of Rh(Phebox) catalysts in asymmetric reductive aldol reaction: High anti-selectivity
Nishiyama, Hisao,Shiomi, Takushi,Tsuchiya, Yasunori,Matsuda, Isamu
, p. 6972 - 6973 (2005)
Chiral rhodium(bisoxazolinylphenyl) complexes (1 mol %) efficiently catalyze the asymmetric reductive aldol reaction of aldehydes and α,β-unsaturated esters at 50 °C for ca. 0.5-1.0 h with several hydrosilanes to give the corresponding β-hydroxypropionates with extremely high anti-selectivity (up to 98%) and enantioselectivity (up to 96% ee). The stereochemical outcome is likely due to a chairlike cyclic transition state involving rhodium-(E)-enolate. Copyright
(Diisopinocampheyl)borane-mediated reductive aldol reactions of acrylate esters: Enantioselective synthesis of anti-aldols
Allais, Christophe,Nuhant, Philippe,Roush, William R.
supporting information, p. 3922 - 3925 (2013/09/02)
The (diisopinocampheyl)borane promoted reductive aldol reaction of acrylate esters 4 is described. Isomerization of the kinetically formed Z(O)-enolborinate 5Z to the thermodynamic E(O)-enolborinate 5E via 1,3-boratropic shifts, followed by treatment with
Efficient preparation of new rhodium- and iridium-[bis(oxazolinyl)-3,5- dimethylphenyl] complexes by C-H bond activation: Applications in asymmetric synthesis
Ito, Jun-Ichi,Shiomi, Takushi,Nishiyama, Hisao
, p. 1235 - 1240 (2007/10/03)
The bis(oxazolinyl)-3,5-dimethylphenylrhodium and -iridium complexes were synthesized in high yields by an efficient C-H bond activation method with 4,6-dimethyl-1,3-bis(oxazolinyl)benzene derivatives. The catalytic activity of the complexes was examined
4-substituted-phenyl(bisoxazoline)-rhodium complexes: Efficiency in the catalytic asymmetric reductive aldol reaction
Shiomi, Takushi,Ito, Jun-Ichi,Yamamoto, Yoshihiko,Nishiyama, Hisao
, p. 5594 - 5600 (2008/02/04)
Electronic effects of the substituents on the phenyl ring of the phenyl(bisoxazoline) ligand skeleton of rhodium catalysts was examined in the asymmetric reductive aldol reactions of acrylates and aldehydes. The electron-withdrawing NO2 group o
The E/Z geometry of the enolate component determines face selection of the aldehyde component in chiral diazaborolidine-directed enantioselective aldol coupling
Corey,Lee
, p. 1737 - 1740 (2007/10/02)
An analysis of the effect of enolate geometry on transition-state energy explains the stereochemistry of aldol reactions of acetate and propionate esters with aldehydes using as reagent the chiral diazaborolidine 1.
NEW PROCESS FOR ENANTIOSELECTIVE NUCLEOPHILIC ADDITION TO ALDEHYDES TO FORM SECONDARY ALCOHOLS
Corey, E. J.,Kim, Sung Soo
, p. 3715 - 3718 (2007/10/02)
New methodology is described for the enantioselective conversion of aldehydes to anti aldols 4 and homoallylic alcohols 7.
