以轴手性的BINOL/H8-BINOL(BINOL为联苯酚)和大位阻的金刚烷酰氯为原料,合成了系列新型手性单齿亚磷酸酯配体,并应用于Cu催化的二乙基锌对环烯酮的不对称1,4.共轭加成反应中.结果表明,配体结构中部分氢化的2,2'-(1,1'-联萘基)亚磷酸酯单元和金刚烷基团,有助于改善反应的对映选择性,对映选择性最高可达79%.
A series of new bulky monophosphite ligands were synthesized from axially chiral BINOL/H8-BINOL (BINOL:1-(2-hydroxynaphthalen-l-yl)naphthalen-2-ol) and highly sterically hindered adamantylcarbonyl chloride.The effectiveness of these ligands was evaluated by the Cu-catalyzed asymmetric 1,4-conjugate addition of diethylzinc to cyclic enones with enantioselectivities of up to 79% ee.The results showed that a ligand structure comprising a partially hydrogenated 2,2'-(l,]'-binaphthyl)phosphite scaffold and an adamantyl moiety was effective in improving the enantioselectivity.
参考文献
| [1] | Alexakis A;Backvall J E;Krause N;Pamies O Dieguez M .[J].Chemical Reviews,2008,108:2796. |
| [2] | Jerphagnon T;Pizzuti M G;Minnaard A J;Feringa B L .[J].Chemical Society Reviews,2009,38:1039. |
| [3] | Feringa B L .[J].Accounts of Chemical Research,2000,33:346. |
| [4] | Rossiter B E;Swingle N M .[J].Chemical Reviews,1992,92:771. |
| [5] | Scafato P;Cunsolo G;Labano S;Rosini C .Asymmetric activation of tropos catalysts in the stereoselective catalytic conjugate additions of R2Zn to alpha,beta-enones: an efficient synthesis of (-)-muscone[J].Tetrahedron,2004(40):8801-8806. |
| [6] | Iuliano A;Scafato P;Torchia R .Deoxycholic acid-based phosphites as chiral ligands in the enantioselective conjugate addition of dialkylzincs to cyclic enones: preparation of (-)-(R)-muscone[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):2533-2538. |
| [7] | Ito K;Eno S;Saito B;Katsuki T .[J].Tetrahedron Letters,2005,46:3981. |
| [8] | Degrado SJ.;Hoveyda AH.;Mizutani H. .Modular peptide-based phosphine ligands-in asymmetric catalysis: Efficient and enantioselective Cu-catalyzed conjugate additions to five-, six-, and seven-membered cyclic enones[J].Journal of the American Chemical Society,2001(4):755-756. |
| [9] | Mizutani H;Degrado S J;Hoveyda A H .[J].Journal of the American Chemical Society,2002,124:779. |
| [10] | Dijk EW;Panella L;Pinho P;Naasz R;Meetsma A;Minnaard AJ;Feringa BL .The asymmetric synthesis of (-)-pumiliotoxin C using tandem catalysis[J].Tetrahedron,2004(43):9687-9693. |
| [11] | Alexakis A;Frutos J C;Mangeney P .[J].TETRAHEDRON-ASYMMETRY,1993,4:2427. |
| [12] | Mata Y;Dieguez M;Pamies O;Biswas K;Woodward S .Sugar-phosphite-oxazoline and phosphite-phosphoroamidite ligand libraries for Cu-catalyzed asymmetric 1,4-addition reactions[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2007(13):1613-1617. |
| [13] | Dieguez M;Ruiz A;Claver C .[J].TETRAHEDRON-ASYMMETRY,2001,12:2861. |
| [14] | Zhang W C;Wang C J;Gao W Z;Zhang X M .[J].Tetrahedron Letters,2005,46:6087. |
| [15] | Liang L;Au-Yeung T T L;Chan A S C .[J].Organic Letters,2002,4:3799. |
| [16] | Liang L;Yan M;Li YM;Chan ASC .Highly enantioselective copper-catalyzed 1,4-conjugate addition of diethylzinc to cyclic enones and alpha,beta-unsaturated lactones[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):2575-2578. |
| [17] | Liang L.;Chan ASC. .Copper-catalyzed highly enantioselective 1,4-conjugate addition of trimethylaluminum to 2-cyclohexenone[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2002(13):1393-1396. |
| [18] | Hu X Q;Chen H L;Zhang X M .[J].Angewandte Chemie International Edition,1999,38:3518. |
| [19] | Hu YC.;Liang XM.;Wang JW.;Zheng Z.;Hu XQ. .Readily prepared chiral P,N Ligands and their applications in Cu-catalyzed enantioselective conjugate additions[J].The Journal of Organic Chemistry,2003(11):4542-4545. |
| [20] | Wan HH.;Hu YC.;Liang YX.;Gao S.;Wang JW.;Zheng Z.;Hu XQ. .Highly enantioselective conjugate addition of diethylzinc to acyclic enones with fine-tunable phosphite-pyridine ligands[J].The Journal of Organic Chemistry,2003(21):8277-8280. |
| [21] | Hu YC.;Liang XM.;Wang JW.;Zheng Z.;Hu XQ. .Highly enantioselective 1,4-conjugate addition of diethylzinc to acyclic enones with chiral phosphite-pyridine ligands derived from H-8-NOBIN[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2003(24):3907-3915. |
| [22] | Wang L L;Li Y M;Yip C W;Qiu L Q Zhou Z Y Chan A S C .[J].Advanced Synthesis and Catalysis,2004,346:947. |
| [23] | Zhao QL;Wang LL;Kwong FY;Chan ASC .Cu-catalyzed enantioselective conjugate addition of diethylzinc to cyclic enones with chiral phosphite ligands derived from 1,2 : 5,6-di-O-cyclohexylidene-D-mannitol[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2007(16):1899-1905. |
| [24] | Reetz, MT;Guo, HC;Ma, JA;Goddard, R;Mynott, RJ .Helical Triskelion Monophosphites as Ligands in Asymmetric Catalysis[J].Journal of the American Chemical Society,2009(11):4136-4142. |
| [25] | Zhang FY.;Chan ASC.;Kwok WH. .A comparison of the asymmetric hydrogenation catalyzed by rhodium complexes containing chiral ligands with a binaphthyl unit and those with a 5,5 ',6,6 ',7,7 ',8,8 '-octahydro-binaphthyl unit[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2001(16):2337-2342. |
| [26] | Wang B;Feng X;Cui X;Liu H,Jiang Y.[J].Chemical Communications,2000:1605. |
| [27] | Zhang FY.;Chan ASC.;Pai CC. .Asymmetric synthesis of chiral amine derivatives through enantioselective hydrogenation with a highly effective rhodium catalyst containing a chiral bisaminophosphine ligand[J].Journal of the American Chemical Society,1998(23):5808-5809. |
| [28] | Zhang FY.;Chan ASC. .Enantioselective conjugate addition of diethylzinc to cyclic enones catalyzed by chiral copper complexes containing a new phosphorus ligand with an H-8-binaphthoxy moiety[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,1998(7):1179-1182. |
| [29] | Chan A S C;Zhang F-Y;Yip C W .[J].Journal of the American Chemical Society,1997,119:4080. |
| [30] | Li X;Jia X;Lu G;Au-Yeung T T L Lam K H Lo T W H Chan A S C .[J].TETRAHEDRON-ASYMMETRY,2003,14:2687. |
| [31] | Liang L;Au-Yeung T T L;Chan A S C .[J].Organic Letters,2002,4:3799. |
| [32] | Guo R;Au-Yeung T T L;Wu J;Choi M C K,Chan A S C .[J].TETRAHEDRON-ASYMMETRY,2002,13:2519. |
| [33] | Zeng Q.;Liu H.;Mi A.;Jiang YH.;Li XS.;Choi MCK.;Chan ASC. .H-8-MonoPhos and its application in catalytic enantioselective hydrogenation of alpha-dehydroamino acids[J].Tetrahedron,2002(43):8799-8803. |
| [34] | 万博,赵庆鲁,王来来.新型手性膦配体的合成及其在1,4-共轭加成反应中的应用[J].催化学报,2010(05):514-517. |
| [35] | Alexakis A;Trevitt G P;Bernardinelli G .[J].Journal of the American Chemical Society,2001,123:4358. |
| [36] | Alexakis A;Benhaim C;Rosset S;Humam M .[J].Journal of the American Chemical Society,2002,124:5262. |
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