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由廉价的手性氨基醇与3,5-二溴或3,5-二碘水杨醛缩合得到配体,配体与VO(acac)2按一定比例络合形成络合物催化剂,考察了室温下该催化剂对芳基甲基硫醚不对称氧化反应的催化性能. 结果表明,当VO(acac)2/配体摩尔比为1/2, 并且以H2O2作为氧源时,催化剂具有较高的活性和中等至很高的对映选择性. 与(S)-苯丙氨醇和(R)-亮氨醇衍生得到的配体相比,由(S)-缬氨醇得到的配体具有更高的对映选择性. 在缓慢滴加H2O2的条件下,以3,5-二碘水杨醛和(S)-缬氨醇缩合得到的Schiff碱为配体,以苯甲硫醚和对溴苯甲硫醚为底物时,产物的ee值分别为88%和92%. 研究表明,与Fe(acac)3/Schiff碱体系不同,向VO(acac)2/Schiff碱催化体系中加入羧酸或羧酸盐类化合物并不能改善催化剂的催化性能.

参考文献

[1] Pitchen P;Dunach E;Deshmukh M N;Kagan H B .[J].Journal of the American Chemical Society,1984,106(26):8188.
[2] Di Furia F;Modena G;Seraglia R.[J].Synthesis-Stuttgart,1984(04):325.
[3] Katsuki T .[J].Coordination Chemistry Reviews,1995,140:189.
[4] Volcho K P;Salakhutdinov N F;Tolstikov A G .[J].Russian Journal of Organic Chemistry,2003,39(11):1537.
[5] Kaczorowska K;Kolarska Z;Mitka K;Kowalski P .[J].Tetrahedron,2005,61(35):8315.
[6] 黄秋亚,朱槿,邓金根.金属催化硫醚的不对称氧化研究进展[J].有机化学,2005(05):496-506.
[7] Bolm C;Bienewald F .[J].Angewandte Chemie International Edition,1996,34(23-24):2640.
[8] Bolm C .[J].Coordination Chemistry Reviews,2003,237(1-2):245.
[9] Liu G;Cogan D A;Ellman J A .[J].Journal of the American Chemical Society,1997,119(41):9913.
[10] Weix D J;Ellman J A .[J].Organic Letters,2003,5(08):1317.
[11] Blum SA.;Bergman RG.;Ellman JA. .Enantioselective oxidation of di-tert-butyl disulfide with a vanadium catalyst: Progress toward mechanism elucidation[J].The Journal of Organic Chemistry,2003(1):150-155.
[12] Legros J;Bolm C;Angew Chem .[J].International Ed,2003,42(44):5487.
[13] Legros J;Bolm C .[J].Angewandte Chemie International Edition,2004,43(32):4225.
[14] Legros J;Bolm C .Investigations on the iron-catalyzed asymmetric sulfide oxidation[J].Chemistry: A European journal,2005(4):1086-1092.
[15] Skarzewski J;Ostrycharz E;Siedlecka R .[J].Tetrahedron:Asymmetry,1999,10(18):3457.
[16] Karpyshev NN.;Talsi EP.;Bryliakov KP.;Tolstikova OV. Tolstikov AG.;Yakovleva OD. .Effect of portionwise addition of oxidant in asymmetric vanadium-catalyzed sulfide oxidation[J].Journal of molecular catalysis, A. Chemical,2000(1/2):91-95.
[17] Sun J T;Zhu Ch J;Dai Zh Y;Yang M H,Pan Y,Hu H W .[J].Journal of Organic Chemistry,2004,69(24):8500.
[18] Vetter A H;Berkessel A .[J].Tetrahedron Letters,1998,39(13):1741.
[19] Jeong Y C;Choi S;Hwang Y D;Ahn K H .[J].Tetrahedron Letters,2004,45(50):9249.
[20] Barbarini A;Maggi R;Muratori M;Sartori G;Sartorio R .Enantioselective sulfoxidation catalyzed by polymer-supported chiral Schiff base-VO(acac)(2) complexes[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2004(16):2467-2473.
[21] Pelotier B.;Anson MS.;Campbell IB.;Macdonald SJF.;Priem G.;Jackson RFW. .Enantioselective sulfide oxidation with H2O2: A solid phase and array approach for the optimisation of chiral Schiff base-vanadium catalysts[J].Synlett,2002(7):1055-1060.
[22] Cogan DA.;Kim KJ.;Backes BJ.;Ellman JA.;Liu GC. .Catalytic asymmetric oxidation of tert-butyl disulfide. Synthesis of tert-butanesulfinamides, tert-butyl sulfoxides, and tert-butanesulfinimines[J].Journal of the American Chemical Society,1998(32):8011-8019.
[23] McKennon M J;Meyers A I;Drauz K;Schwarm M .[J].Journal of Organic Chemistry,1993,58(13):3568.
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