220959-45-5Relevant academic research and scientific papers
Enantioselective Allylic Oxidation Catalyzed by Chiral Bisoxazoline-Copper complexes
Gokhale, Abha S.,Minidis, Alexander B. E.,Pfaltz, Andreas
, p. 1831 - 1834 (1995)
Copper(I) complexes prepared in situ from chiral bisoxazolines and Cu(II)OTf have been studied as catalysts for the allylic oxidation of cycloalkenes.Using 5 molpercent of catalyst and tert-butyl perbenzoate as oxidant, optically active 2-cycloalkenyl ben
Asymmetric peroxidation of prochiral allylic and benzylic compounds with tert-butyl hydroperoxide and chiral bisoxazoline-copper complexes
Schulz, Manfred,Kluge, Ralph,Gadissa Gelalcha, Feyissa
, p. 4341 - 4360 (2007/10/03)
The first enantioselective peroxidation of prochiral allylic and benzylic C-H compounds by the use of chiral bisoxazoline-copper(I) complexes, generated in situ from the ligands 3 and 4a-d, and t-BuOOH as oxidant is reported. Cyclohexene 1, cyclopentene 5, α-angelica lactone 7, allylbenzene 9 and 2-phenylbutane 11 were converted into the optically active allylic and benzylic tert-butyl peroxides 2, 6, 8, 10a and 12 in good yields and ee values of 4-20%. Oxidations of 1-substituted 1-cyclohexenes 13a-c led to mixtures of regioisomeric peroxides 16a-c, 17a-c and 18a-c with different regio- and enantioselectivities, depending on the 1-substituent and the ligand used. The highest ee values (up to 84%) were observed for (S)-3-tert- butylperoxy-1-methyl-1-cyclohexene 17a.
