以轴手性联萘酚为原料,合成了一系列手性磷酸催化剂,并首次将其应用于催化芳香胺和硝基烯烃的不对称氮杂迈克尔加成反应中,产物β-硝基胺的产率和对映选择性分别达65％～95％和16％～70％.
Chiral phosphoric acid was found to be an effective organocatalyst in the enantioselective aza-Michael addition of aromatic amines to nitroolefms giving the corresponding β-nitroarnine products in good yields (65％-95％) with moderate to good enantiomeric excesses (16％-70％).This study represents the first example of a chiral phosphoric acid catalyzed asymmetric aza-Michael addition reaction.
参考文献
| [1] | Baer H H;Urbas L;Patai S.The Chemistry of the Nitro and Nitroso Group[M].New York:Interscience Publishers,1969:117. |
| [2] | Marqués-López E;Merino P;Tejero T;Herrera R P.[J].European Journal of Organic Chemistry,2009:2401. |
| [3] | Arrayás R G;Carretero J C .[J].Chemical Society Reviews,2009,38:1940. |
| [4] | Westermann B .[J].Angewandte Chemie International Edition,2003,42:151. |
| [5] | Xu L W;Xia C G.[J].European Journal of Organic Chemistry,2005:633. |
| [6] | Enders D;Wang C;Liebich J X .[J].Chemistry-A European Journal,2009,15:11058. |
| [7] | Weiner B;Szyma(n)ski W;Janssen D B;Minnaarda A J Feringa B L .[J].Chemical Society Reviews,2010,39:1656. |
| [8] | Kawatsura M.;Hartwig JF. .Palladium-catalyzed intermolecular hydroamination of vinylarenes using arylamines[J].Journal of the American Chemical Society,2000(39):9546-9547. |
| [9] | Fadini L;Togni A.[J].Chemical Communications,2003:30. |
| [10] | Zhuang W;Hazell R G;Jφrgensen K A.[J].Chemical Communications,2001:1240. |
| [11] | Li K;Hii K K.[J].Chemical Communications,2003:1132. |
| [12] | Phua P H;White A J P;de Vries J G;Hii K K .[J].Advanced Synthesis and Catalysis,2006,348:587. |
| [13] | Phua PH;Mathew SP;White AJP;de Vries JG;Blackmond DG;Hii KK .Elucidating the mechanism of the asymmetric aza-Michael reaction[J].Chemistry: A European journal,2007(16):4602-4613. |
| [14] | Hamashima Y;Somei H;Shimura Y;Tamura T Sodeoka M .[J].Organic Letters,2004,6:1861. |
| [15] | Reboule, I;Gil, R;Collin, J .Enantioselective conjugate addition of aromatic amines to N-alkenoyloxazolidinones catalyzed by iodido(binaphtholato)samarium[J].European journal of organic chemistry,2008(3):532-539. |
| [16] | Scettri A;Massa A;Palombi L;Villano R;Acocella MR .Organocatalytic asymmetric aza-Michael addition of aniline to chalcones under solvent-free conditions[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2008(18):2149-2152. |
| [17] | Lucet D;Le Gall T;Mioskowski C .[J].Angewandte Chemie International Edition,1998,37:2580. |
| [18] | Lucet D;Toupet L;Le Gall T;Mioskowski C .[J].Journal of Organic Chemistry,1997,62:2682. |
| [19] | Tureoni J;Lebeau L;Paris J M;Mioskowski C .[J].Tetrahedron Letters,2006,47:121. |
| [20] | Turconi J;Lebeau L;Paris JM;Mioskowski C .Stereoselective synthesis of trifluoromethyl-substituted 1,2diamines by aza-Michael reaction with trans-3,3,3-trifluoro-1-nitropropene[J].Tetrahedron,2006(34):8109-8114. |
| [21] | Uraguchi D;Nakashima D;Ooi T .[J].Journal of the American Chemical Society,2009,131:7242. |
| [22] | List B .[J].Tetrahedron,2002,58:5573. |
| [23] | Schreiner P R .[J].Chemical Society Reviews,2003,32:289. |
| [24] | Pihko P M .[J].Angewandte Chemie International Edition,2004,43:2062. |
| [25] | Doyle A G;Jacobsen E N .[J].Chemical Reviews,2007,107:5713. |
| [26] | Yu X;Wang W .[J].Chemistry-An Asian Journal,2008,3:516. |
| [27] | Connon S J .[J].Angewandte Chemie International Edition,2006,45:3909. |
| [28] | Akiyama T .[J].Chemical Reviews,2007,107:5744. |
| [29] | Adair G;Mukherjee S;List B .[J].Aldrichimica Acta,2008,41:31. |
| [30] | Terada M .Binaphthol-derived phosphoric acid as a versatile catalyst for enantioselective carbon-carbon bond forming reactions[J].Chemical communications,2008(35):4097-4112. |
| [31] | Yang L;Zhu Q;Guo S;Qian B Xia C Huang H .[J].Chemistry-A European Journal,2010,16:1638. |
| [32] | Xie Y;Zhao Y;Qian B;Yang L,Xia C,Huang H .[J].Angewandte Chemie International Edition,2011,50:5682. |
| [33] | Xu L W;Xia C G;Hu X.[J].Chemical Communications,2003:2570. |
| [34] | Xu LW;Xia CG .TMSCl-promoted transition metal-catalyzed aza-Michael reactions of chalcones with carbamates[J].Synthesis: International Journal of Methods in Synthetic Organic Chemistry,2004(13):2191-2195. |
| [35] | Yang L;Xu L W;Xia C G .[J].Tetrahedron Letters,2005,46:3279. |
| [36] | Yang L;Xu L W;Zhou W;Li L,Xia C G .[J].Tetrahedron Letters,2006,47:7723. |
| [37] | Yang L;Xu L W;Xia C G .[J].Tetrahedron Letters,2007,48:1599. |
上一张
下一张
上一张
下一张
计量
- 下载量()
- 访问量()
文章评分
- 您的评分：
-
10%
-
20%
-
30%
-
40%
-
50%