将手性二茂铁双膦配体ImiFerroPhos应用到β-取代-α,β-不饱和磷酸酯的不对称氢化反应中,在温和的反应条件下,以高收率及较高对映选择性合成了一系列β-取代的手性磷酸酯,最高获得了92%的ee值.
参考文献
[1] | Hilderbrand R L.The Role of Phosphonates in Living Systems[M].Boca Raton:CRC Press,1983 |
[2] | Bellucci C;Gualtieri F;Scapecchi S;Teodori E,Budriesi R,Chiarini A .[J].Farmaco,1989,44:1167. |
[3] | Kafarski P;Lejczak B .[J].Phosphorus, Sulfur, and Silicon and the Related Elements,1991,63:193. |
[4] | Jung K W;Janda K D;Sanfilippo P J;Wachter M .[J].Bioorganic & Medicinal Chemistry Letters,1996,6:2281. |
[5] | Lo C H L;Wentworth P Jr;Jung K W;Yoon J,Ashley J A,Janda K D .[J].Journal of the American Chemical Society,1997,119:10251. |
[6] | Datta A;Wentworth P Jr;Shaw J P;Simeonov A,Janda K D .[J].Journal of the American Chemical Society,1999,121:10461. |
[7] | Kafarski P;Lejczak B .[J].Current Medicinal Chemistry - Anti-Cancer Agents,2001,1:301. |
[8] | Kolodiazhnyi OI .Asymmetric synthesis of hydroxyphosphonates[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2005(20):3295-3340. |
[9] | Kelly S E;Trost B M;Fleming I.Comprehensive Organic Synthesis[M].Oxford:Pergamon Press,1991:761. |
[10] | Savignac P;lorga B.Morden Phosphonate Chemistry[M].Boca Raton:CRC Press,2003 |
[11] | Omelanzcuk J;Sopchik A E;Lee S G;Akutagawa K,Cairns S M,Bentrude W G .[J].Journal of the American Chemical Society,1988,110:6908. |
[12] | Cairns S M;Bentrude W G .[J].Tetrahedron Letters,1989,30:1025. |
[13] | Denmark S E;Chen C T .[J].Journal of the American Chemical Society,1995,117:11879. |
[14] | Kranz M.;Denmark SE. .AN AB INITIO STUDY OF THE P-C BOND ROTATION IN PHOSPHORUS(V)-STABILIZED CARBANIONS - THE PHOSPHORYL VERSUS THIOPHOSPHORYL GROUP[J].The Journal of Organic Chemistry,1995(18):5867-5877. |
[15] | Bennani YL.;Hanessian S. .THE ASYMMETRIC SYNTHESIS OF ALPHA-SUBSTITUTED ALPHA-METHYL AND ALPHA-PHENYL PHOSPHONIC ACIDS - DESIGN, CARBANION GEOMETRY, REACTIVITY AND PREPARATIVE ASPECTS OF CHIRAL ALKYL BICYCLIC PHOSPHONAMIDES [Review][J].Tetrahedron,1996(44):13837-13866. |
[16] | Bhanthumnavin W.;Bentrude WG.;Arif A. .Photo-Arbuzov rearrangements of benzylic phosphites. Stereochemistry at migratory carbon[J].The Journal of Organic Chemistry,1998(22):7753-7758. |
[17] | Goulioukina NS.;Beletskaya IP.;Henry JC.;Lavergne D. Ratovelomanana-Vidal V.;Genet JP.;Dolgina TM. .A practical synthetic approach to chiral alpha-aryl substituted ethylphosphonates[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2001(2):319-327. |
[18] | Goulioukina NS.;Dolgina TM.;Bondarenko GN.;Beletskaya IP.;Ilyin MM. Davankov VA.;Pfaltz A. .Highly enantioselective hydrogenation of alpha,beta-unsaturated phosphonates with iridium-phosphinooxazoline complex: synthesis of a phosphorus analogue of naproxen[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2003(10):1397-1401. |
[19] | Hayashi T;Senda T;Takaya Y;Ogasawara M .[J].Journal of the American Chemical Society,1999,121:11591. |
[20] | Duan Z C;Hu X P;Wang D Y;Yu S B,Zheng Z .[J].Tetrahedron Letters,2009,50:6720. |
[21] | Konno, T.;Shimizu, K.;Ogata, K.;Fukuzawa, S.-I. .Rhodium-catalyzed enantioselective hydrogenation of unsaturated phosphonates by ClickFerrophos ligands[J].The Journal of Organic Chemistry,2012(7):3318-3324. |
[22] | Noyori R.Asymmetric Catalysis in Organic Synthesis[M].New York:Wiley,1994 |
[23] | Jacobsen E N;Pfaltz A;Yamamoto H.Comprehensive Asymmetric Catalysis[M].Berlin:Springer-Verlag,1999 |
[24] | Ojima I.Catalytic Asymmetric Synthesis[M].New York:Wiley-VCH,2000 |
[25] | Tang W J;Zhang X M .[J].Chemical Reviews,2003,103:3029. |
[26] | de Vries J G;Elsevier C J.The Handbook of Homogeneous Hydrogenation[M].Weinheim:Wiley-VCH,2007 |
[27] | Minnaard A J;Feringa B L;Lefort L;de Vries J G .[J].Accounts of Chemical Research,2007,40:1267. |
[28] | Sun H J;Pan Y J;Li S H;Zhang Y X,Dong Y Y,Liu S C,Liu Z Y .[J].Journal of Energy Chemistry,2013,22:710. |
[29] | Chen P R;Chew L M;Kostka A;Xie K P,Muhler M,Xia W .[J].Journal of Energy Chemistry,2013,22:312. |
[30] | Duan Z C;Hu X P;Wang D Y;Huang J D,Yu S B,Deng J,Zheng Z .[J].Advanced Synthesis & Catalysis,2008,350:1979. |
[31] | Duan, Z.-C.;Wang, L.-Z.;Song, X.-J.;Hu, X.-P.;Zheng, Z. .Enantioselective synthesis of optically active alkylphosphonates via Rh-catalyzed asymmetric hydrogenation of β-substituted α,β- unsaturated phosphonates[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2012(6/7):508-514. |
[32] | Duan Z C;Hu X P;Zhang C;Wang D Y,Yu S B,Zheng Z .[J].Journal of Organic Chemistry,2009,74:9191. |
[33] | Luo, L.-B.;Wang, D.-Y.;Zhou, X.-M.;Zheng, Z.;Hu, X.-P. .Asymmetric synthesis of 2-alkyl-3-phosphonopropanoic acid derivatives via Rh-catalyzed asymmetric hydrogenation[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2011(24):2117-2123. |
[34] | Wang, DY;Hu, XP;Hou, CJ;Deng, J;Yu, SB;Duan, ZC;Huang, JD;Zheng, Z .Enantioselective Rh-Catalyzed Hydrogenation of 3-Aryl-2-phosphonomethylpropenoates by a New Class of Chiral Ferrocenyl Diphosphine Ligands[J].Organic letters,2009(15):3226-3229. |
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