243860-98-2Relevant academic research and scientific papers
Enantioenriched (S)-6,6′-diphenylBinol-Ca: A novel and efficient chirally modified metal complex for asymmetric epoxidation of α,β-unsaturated enones
Kumaraswamy,Sastry,Jena, Nivedita,Kumar, K. Ravi,Vairamani
, p. 3797 - 3803 (2003)
A novel enantioenriched-Ca complex was generated using low cost commercially available CaCl2 and the potassium salt of (S)-6,6′-diphenylBINOL and its application to α,β-unsaturated enone epoxidation is described. Furthermore the absolute stereo
Chiral octahedral complexes of Co(iii) as catalysts for asymmetric epoxidation of chalcones under phase transfer conditions
Larionov, Vladimir A.,Markelova, Elina P.,Smol'yakov, Alexander F.,Savel'yeva, Tat'yana F.,Maleev, Victor I.,Belokon, Yuri N.
, p. 72764 - 72771 (2015/09/15)
Stereochemically inert and positively charged chiral complexes of Co(iii) were shown to catalyze the asymmetric epoxidation of chalcones with H2O2 under phase transfer conditions. The reaction products had enantiomeric purities of up to 55%. It was also shown that complex 1a I- catalyzed the coupling reaction of a resulting epoxide with CO2 (conversion 72%).
Kinetic resolution of 2,3-epoxy 3-aryl ketones via catalytic asymmetric ring-opening with pyrazole derivatives
Huang, Tianyu,Lin, Lili,Hu, Xiaolei,Zheng, Jianfeng,Liu, Xiaohua,Feng, Xiaoming
supporting information, p. 11374 - 11377 (2015/08/18)
A highly efficient catalytic kinetic resolution of 2,3-epoxy 3-aryl ketones via asymmetric ring-opening with pyrazole derivatives has been achieved by using a chiral N,N′-dioxide-Sc(III) complex as the catalyst. A wide variety of substrates were readily scoped, and the selectivity factors obtained were excellent (up to >300).
Stereocontrolled ring-opening of some enantiomerically enriched epoxy ketones and epoxy alcohols using trimethylaluminium: Synthesis of (S)-2-arylpropanoic acids
Carde, Lydia,Davies, D. Huw,Roberts, Stanley M.
, p. 2455 - 2463 (2007/10/03)
Poly-(D)-leucine-catalysed epoxidation of chalcone furnished epoxide (+)-6; treatment of this epoxide with trimethylaluminium followed by zinc borohydride reduction and oxidative cleavage furnished (S)-2-phenylpropanoic acid 11. In a complementary sequence epoxy ketones (-)-6 and 25 were converted into (S)-2-phenylpropanoic acid and (S)-fenoprofen 5 respectively by reduction with zinc borohydride, reaction with trimethylaluminium and oxidative cleavage. Similarly epoxy ketones (-)-6, 21 and 28 were treated with methylmagnesium iodide, trimethylaluminium and the resultant alcohols subjected to oxidative cleavage to afford (S)-2-phenylpropanoic acid (from the first two substrates) and (S)-naproxen 1.
PaaSicats: Powerful catalysts for asymmetric epoxidation of enones. Novel syntheses of α-arylpropanoic acids including (S)-fenoprofen
Carde, Lydia,Davies, Huw,Geller, Thomas P.,Roberts, Stanley M.
, p. 5421 - 5424 (2007/10/03)
Application of the recently developed silica-adsorbed polyleucine catalysts to the enantioselective epoxidation of two enones is reported. Treatment of these epoxides with trimethylaluminium in moist dichloromethane generates the α-hydroxy-β-methylketones, with inversion of configuration. Diastereoselective reduction of the ketone moiety followed by oxidative cleavage generates α-arylpropanoic acids.
