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OALib Journal期刊
ISSN: 2333-9721
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金属催化芳基硼酸与酮不对称1,2-加成反应研究进展有机化学
DOI: 10.6023/cjoc201305044, PP. 2298-2309
Keywords: 金属催化,芳基硼酸,酮,不对称,1,2-加成,研究进展
Abstract:
许多具有生物活性的天然产物及药物均含有手性芳基叔醇结构单元，金属催化芳基硼酸与酮不对称1，2-加成反应是合成该类化合物的有效方法.由于芳基硼酸具有官能团兼容性好、对水及空气稳定、低毒等优点，近来已经成为化学家研究的热点.就近年来金属催化芳基硼酸与活泼酮如靛红、三氟甲基酮、α-酮酯及1，2-二酮和不活泼酮的不对称1，2-加成的研究进展做一详细综述.
| [1] | For reviews,see: (a) Jacobsen,E.N.; Pfaltz,A.; Yamamoto,H.Comprehensive Asymmetric Catalysis,1 st ed.,Springer,Berlin,1999.
|
| [2] | (c) Fagnou,K.; Lautens,M.Chem.Rev.2003,103,169.
|
| [3] | (e) Garcia,C.; Martin,V.S.Curr.Org.Chem.2006,10,1849.
|
| [4] | (g) Tian,P.; Dong,H.-Q.; Lin,G.-Q.ACS Catal.2011,95.
|
| [5] | (b) de Clercq,E.Rev.Med.Virol.2009,19,287.
|
| [6] | (d) Julian,L.; Wang,D.Z.; Bostick,T.; Caille,S.; Choi,R.; DeGraffenreid,M.; Di,Y.; He,X.; Hungate,R.W.; Jaen,J.C.; Liu,J.; Monshouwer,M.; McMinn,D.; Rew,Y.; Sudom,A.; Sun,D.; Tu,H.; Ursu,S.; Walker,N.; Yan,X.; Ye,Q.; Powers,J.P.J.Med.Chem.2008,51,3953.
|
| [7] | (e) Kopecky,D.J.; Jiao,X.Y.; Fisher,B.; McKendry,S.; Labelle,M.; Piper,D.E.; Coward,P.; Shiau,A.K.; Escaron,P.; Danao,J.; Chai,A.; Jaen,J.; Kayser,F.Bioorg.Med.Chem.Lett.2012,22,2407.
|
| [8] | (b) Li,C.-J.; Meng,Y.J.Am.Chem.Soc.2000,122,9538.
|
| [9] | (b) Huang,W.-S.; Hu,Q.-S.; Pu,L.J.Org.Chem.1999,64,7940.
|
| [10] | (e) Montserrat,F.; Xavier,V.; Lluis,S.; Miquel,A.P.; Antoni,R.J.Org.Chem.2004,69,2532.
|
| [11] | Tomita,D.; Wada,R.; Kanai,M.; Shibasaki,M.J.Am.Chem.Soc.2005,127,4138.
|
| [12] | Sakai,M.; Ueda,M.; Miyaura,N.Angew.Chem.,Int.Ed.1998,37,3279.
|
| [13] | (b) Focken,T.; Rudolph,J.; Bolm,C.Synthesis 2005,429.
|
| [14] | (d) Suzuki,K.; Kondo,K.; Aoyama,T.Synthesis 2006,1360.
|
| [15] | (f) Duan,H.F.; Xie,J.H.; Shi,W.J.; Zhang,Q.; Zhou,Q.L.Org.Lett.2006,8,1479.
|
| [16] | (h) No€el,T.; Vandyck,K.; Van der Eycken,J.Tetrahedron 2007,63,12961.
|
| [17] | (j) Clarke,E.F.; Rafter,E.; M€uller-Bunz,H.; Higham,L.J.; Gilheany,D.G.J.Organomet.Chem.2011,696,3608.
|
| [18] | Using nickel catalysis: (a) Arao,T.; Kondo,K.; Aoyama,T.Tetrahedron Lett.2007,48,4115.
|
| [19] | (c) Sakupai,F.; Kondo,K.; Aoyama,T.Chem.Pharm.Bull.2009,57,511.
|
| [20] | Using copper catalysis: Tomita,D.; Kanai,M.; Shibasaki,M.Chem.Asian J.2006,1,161.
|
| [21] | (b)Yamamoto,Y.; Shirai,T.; Watanabe,M.; Kurihara,K.; Miyaura,N.Molecules 2011,16,5020.
|
| [22] | (d) Li,K.; Hu,N.-F.; Luo,R.-S.; Yuan,W.-C.; Tang,W.J.Org.Chem.2013,78,6350.
|
| [23] | Luo,F.; Pan,C.D.; Cheng,J.Chin.J.Org.Chem.2010,30,633 (in Chinese).(罗芳,潘长多,成江,有机化学,2010,30,633.)
|
| [24] | (b) Toullec,P.Y.; Jagt,R.B.C.; de Vries,J.G.; Feringa,B.L.; Minnaard,A.J.Org.Lett.2006,8,2715.
|
| [25] | (d) Martina,S.L.X.; Jagt,R.B.C.; de Vries,J.G.; Feringa,B.L.; Minnaard,A.J.Chem.Commun.2006,4093.
|
| [26] | (f) Cai,F.; Pu,X.; Qi,X.; Lynch,V.; Radha,A.; Ready,J.M.J.Am.Chem.Soc.2011,133,18066.
|
| [27] | Jagt,R.B.C.; Toullec,P.Y.; de Vries,J.G.; Feringa,B.L.; Minnaard,A.J.Org.Biomol.Chem.2006,4,773.
|
| [28] | Ackermann,L.Modern Arylation Methods,Wiley-VCH,Wein-heim,Germany,2009,pp.271～310.
|
| [29] | Gui,J.Y.; Chen,G.H.; Cao,P.; Liao,J.Tetrahedron: Asymmetry 2012,23,554.
|
| [30] | (b) Yamamoto,Y.; Shirai,T.; Watanabe,M.; Kurihara,K.; Miyaura,N.Molecules 2011,16,5020.
|
| [31] | Yamamoto,Y.; Yohd,M.; Shirai,T.; Ito,H.; Miyaura,N.Chem.Asian J.2012,7,2246.
|
| [32] | (b) Diez-Gonzalez,S.; Kaur,H.; Zinn,F.K.; Stevens,E.D.; Nolan,S.P.J.Org.Chem.2005,70,4784.
|
| [33] | (e) Jurkauskas,V.; Sadighi,J.P.; Buchwald,S.L.Org.Lett.2003,5,2417.
|
| [34] | Shintani,R.; Takatsu,K.; Hayashi,T.Chem.Commun.2010,46,6822.
|
| [35] | Martina,S.L.X.; Jagt,R.B.C.; Vries,J.G.; Feringa B.L.; Minnaard,A.J.Chem.Commun.2006,4093.
|
| [36] | Jumde,V.R.; Facchetti,S.; Iuliano,A.Tetrahedron: Asymmetry 2010,21,2775.
|
| [37] | (a) Kiesewetter,D.O.; Silverton,J.V.; Eckelman,W.C.J.Med.Chem.1995,38,1711.
|
| [38] | (c) Skaddan,M.B.; Kilbourn,M.R.; Snyder,S.E.; Sherman,P.S.; Desmond,T.J.; Frey,K.A.J.Med.Chem.2000,43,4552.
|
| [39] | (a) He,P.; Lu,Y.; Hu,Q.-S.Tetrahedron Lett.2007,48,5283.
|
| [40] | Duan,H.-F.; Xie,J.-H.Qiao,X.-C.Wang,L.-X.; Zhou,Q.-L.Angew.Chem.,Int.Ed.2008,47,4351.
|
| [41] | (a) Jin,S.-S.; Wang,H.; Xu,M.-H.Chem.Commun.2011,47,7230.
|
| [42] | (c) Thaler,T.; Guo,L.-N.; Steib,A.K.; Raducan,M.; Karaghiosoff,K.; Mayer,P.; Knochel,P.Org.Lett.2011,13,3182.
|
| [43] | (e) Chen,G.; Gui,J.; Li,L.; Liao,J.Angew.Chem.,Int.Ed.2011,50,7681.
|
| [44] | (g) Xue,F.; Li,X.; Wan,B.J.Org.Chem.2011,76,7256.
|
| [45] | Zhu,T.-S.; Jin,S.-S.; Xu,M.-H.Angew.Chem.,Int.Ed.2012,51,780.
|
| [46] | Singh,S.B.; Zink,D.L.; Quamina,D.S.; Pelaez,F.; Teran,A.; Felock,P.; Hazuda,D.J.Tetrahedron Lett.2002,43,2351.
|
| [47] | Feng,X.Q.; Nie,Y.Z.; Yang,J.; Du,H.F.Org.Lett.2012,14,624.
|
| [48] | Gallego,G.M.; Sarpong,R.Chem.Sci.2012,3,1338.
|
| [49] | Bouffard,J.; Itami,K.Org.Lett.2009,11,4410.
|
| [50] | Liao,Y.-X.; Xing,C.-H.; Hu,Q.-S.Org.Lett.2012,14,1544.
|
| [51] | (b) Pu,L.; Yu,H.-B.Chem.Rev.2001,101,757.
|
| [52] | (d) Denmark,S.E.; Fu,J.Chem.Rev.2003,103,2763.
|
| [53] | (f) Riant,O.; Hannedouche,J.Org.Biomol.Chem.2007,5,873.
|
| [54] | (a) Romero,D.L.Ann.Rep.Med.Chem.1994,29,123.
|
| [55] | (c) Wan,Z.-K.; Chenail,E.; Li,H.-Q.; Kendall,C.; Wang,Y.; Gingras,S.; Xiang,J.; Massefski,W.W.; Mansour,T.S.; Saiah,E.J.Org.Chem.2011,76,7048.
|
| [56] | (a) Marshall,R.L.; Muderawan,I.W.; Young,D.J.J.Chem.Soc.,Perkin Trans.2 2000,957.
|
| [57] | (a) Dosa,P.I.; Ruble,J.C.; Fu,G.C.J.Org.Chem.1997,62,444.
|
| [58] | (c) Bolm,C.; Hermanns,N.; Hildebrand,J.P.; Muniz,K.Angew.Chem.,Int.Ed.2000,39,3465.
|
| [59] | (d) Bolm,C.; Rudolph,J.J.Am.Chem.Soc.2002,124,14850.
|
| [60] | (f) Braga,A.L.; Lüdtke,D.S.; Vargas,F.; Paixao,M.W.A.Chem.Commun.2005,19,2512.
|
| [61] | Weber,B.; Seebach,D.Tetrahedron 1994,50,7473.
|
| [62] | Using rhodium catalysis: (a) Sakai,M.; Ueda,M.; Miyaura,N.Angew.Chem.,Int.Ed.1998,37,3279.
|
| [63] | (c) Suzuki,K.; IshⅡ,S.; Kondo,K.; Aoyama,T.Synlett 2006,648.
|
| [64] | (e) Arao,T.; Suzuki,K.; Kondo,K.; Aoyama,T.Synthesis 2006,3809.
|
| [65] | (g) Jagt,R.B.C.; Toullec,P.Y.; de Vries,J.G.; Feringa,B.L.; Minnaard,A.J.Org.Biomol.Chem.2006,4,773.
|
| [66] | (i) Nishimura,T.; Kumamoto,H.; Nagaosa,M.; Hayashi,T.Chem.Commun.2009,5713.
|
| [67] | Using cobalt catalysis: Karthikeyan,J.; Jeganmohan,M.; Cheng,C.-H.Chem.Eur.J.2010,16,8989.
|
| [68] | (b) Yamamoto,K.; Tsurumi,K.; Sakurai,F.; Kondo,K.; Aoyama,T.Synthesis 2008,3585.
|
| [69] | (d) Sakurai,F.; Kondo,K.; Aoyama,T.Tetrahedron Lett.2009,50,6001.
|
| [70] | Using ruthenium catalysis: (a) Yamamoto,Y.; Kurihara,K.; Miyaura,N.Angew.Chem.,Int.Ed.2009,48,4414.
|
| [71] | (c) Yamamoto,Y.; Shirai,T.; Miyaura,N.Chem.Commun.2012,48,2803.
|
| [72] | Zhang,R.; Xu,Q.; Zhang,X.; Zhang,T.; Shi,M.Tetrahedron: Asymmetry 2010,21,1928.
|
| [73] | (a) Shintani,R.; Inoue,M.; Hayashi,T.Angew.Chem.,Int.Ed.2006,45,3353.
|
| [74] | (c) Shintani,R.; Takatsu,K.; Hayashi,T.Chem.Commun.2010,46,6822.
|
| [75] | (e) Duan,H.F.; Xie,J.H.; Qiao,X.C.; Wang,L.X.; Zhou,Q.L.Angew.Chem.,Int.Ed.2008,47,4351.
|
| [76] | (g) Zhu,T.-S.; Jin,S.-S.; Xu,M.-H.Angew.Chem.,Int.Ed.2012,51,780.
|
| [77] | (h) Feng,X.; Nie,Y.; Yang,J.; Du,H.Org.Lett.2012,14,624.
|
| [78] | Toullec,P.Y.; Jagt,R.B.C.; Vries,J.G.; Feringa,B.L.; Min-naard,A.J.Org.Lett.2006,8,2715.
|
| [79] | Shintani,R.; Inoue,M.; Hayashi,T.Angew.Chem.,Int.Ed.2006,45, 3353.
|
| [80] | Lai,H.S.; Huang,Z.Y.; Wu,Q.; Qin,Y.J.Org.Chem.2009,74,283.
|
| [81] | (a) Yamamoto,Y.; Kurihara,K.; Miyaura,N.Angew.Chem.,Int.Ed.2009,48,4414.
|
| [82] | (c) Yamamoto,Y.; Shirai,T.; Miyaura,N.Chem.Commun.2012,48,2803.
|
| [83] | (a) Kaur,H.; Zinn,F.K.; Stevens,E.D.; Nolan,S.P.Organometallics 2004,23,1157.
|
| [84] | (c) Lebel,H.; Davi,M.; Diez-Gonzalez,S.; Nolan,S.P.J.Org.Chem.2007,72,144.
|
| [85] | (d) Laitar,D.S.; Tsui,E.Y.; Sadighi,J.P.J.Am.Chem.Soc.2006,128,11036.
|
| [86] | (f) Laitar,D.S.; Müller,P.; Sadighi,J.P.J.Am.Chem.Soc.2005,127,17196.
|
| [87] | Liu,Z.; Gu,P.; Shi,M.; McDowell,P.; Li,G.G.Org.Lett.2011,13,2314.
|
| [88] | Luo,R.-S.; Li,K.; Hu,Y.L.; Tang,W.J.Adv.Synth.Catal.2013,355,1297.
|
| [89] | (b) Kiesewetter,D.O.; Carson,R.E.; Jagoda,E.M.; Endres,C.J.; Der,M.G.; Herscovitch,P.; Eckelman,W.C.Bioorg.Med.Chem.1997,5,1555.
|
| [90] | (d) Selent,J.; Brandt,W.; Pamperin,D.Goeber,B.Bioorg.Med.Chem.2006,14,1729.
|
| [91] | (b) He,P.; Lu,Y.; Dong,C.-G.; Hu,Q.-S.Org.Lett.2007,9,343.
|
| [92] | Xie,J.-H.; Zhu,S.-F.; Zhou,Q.-L.Chem.Soc.Rev.2012,41,4126.
|
| [93] | Cai,F.; Pu,X.T.; Qi,X.B.; Lynch,V.; Radha,A.; Ready,J.M.J.Am.Chem.Soc.2011,133,18066.
|
| [94] | (b) Qi,W.-Y.; Zhu,T.-S.; Xu,M.-H.Org.Lett.2011,13,3410.
|
| [95] | (d) Feng,X.Wang,Y.; Wei,B.; Yang,J.; Du,H.Org.Lett.2011,13,3300.
|
| [96] | (f) Feng,X.; Wei,B.; Yang,J.; Du,H.Org.Biomol.Chem.2011,9,5927.
|
| [97] | (h) Wang,Y.; Feng,X.; Du,H.Org.Lett.2011,13,4954.
|
| [98] | Jung,J.-K.; Johnson,B.R.; Duong,T.; Decaire,M.; Uy,J.; Gharbaoui,T.; Boatman,P.D.; Sage,C.R.; Chen,R.; Richman,J.G.; Connolly,D.T.; Semple,G.J.Med.Chem.2007,50,1445.
|
| [99] | Ganci,G.R.; Chisholm,J.D.Tetrahedron Lett.2007,48,8266.
|
| [100] | Liu,G.X.; Lu,X.Y.J.Am.Chem.Soc.2006,128,16504.
|
| [101] | Low,D.W.; Pattison,G.; Wieczysty,M.D.; Churchill,G.H.; Lam,H.W.Org.Lett.2012,14,2548.
|
| [102] | Korenaga,T.; Ko,A.; Uotani,K.; Tanaka,Y.; Sakai,T.Angew.Chem.,Int.Ed.2011,50,10703.
|
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