欢迎登录材料期刊网

材料期刊网

高级检索

Rh催化的[5+2]反应是一类高效快速构筑多官能团化七元环的重要方法。介绍了常用的Rh催化剂及其配体;分别基于乙烯基环丙烷(VCP)和劳腾施特劳赫中间体类型的Rh催化[5+2]反应;Rh催化的[5+2]反应机理;Rh催化的[5+2]反应在复杂天然产物合成中的应用。

The rhodium-catalyzed [5+2] cycloaddition reaction is an important methodology in rapid and efficient synthesis of a variety of multifunctional seven-membered ring. Introduced in this review were common rhodium-catalysts, catalyzed [5+2] cycloaddition reactions, the mechanism involved and potential applications in the synthesis of natural products.

参考文献

[1] Sarel S;Breuer E .A novel conjugative 1,5-addition reaction involving the vinylcyclopropane system[J].Journal of the American Chemical Society,1959,81(24):6522-6523.
[2] Pasto D J;Borchardt J K;Fehlner T P;Baney H F et al.Analysis of the reactivity of alkenylidenecyclopropanes in cycloaddition reactions[J].Journal of the American Chemical Society,1976,98(2):526-529.
[3] Sarel S;Felzenstein A;Yovell J.Alternative modes of addition of dienophiles to vinylcyclopropane systems[J].Journal of the Chemical Society, Chemical Communi-cations,1973:859-860.
[4] Sarel S;Felzenstein A;Yovell J.Intramolecular [3+4] cycloaddition in substituted dispiro[2,3,x]alkanes. A new pathway to polycyclic olefins containing cycloheptene[J].Journal of the Chemical Society, Chemical Communi-cations,1974:753-754.
[5] Felzenstein A;Sarel S;Yovell J.Uncatalysed olefin metathesis reaction[J].Journal of the Chemical Society, Chemical Communications,1975:918-919.
[6] Fowler F W .Synthesis and thermolysis ofN-Methoxy-carbonyl-2,3-homopyrrole[J].Angewandte Chemie Inter-national Edition in English,1971,10(2):135-137.
[7] Jason Reed Hudlicky;John Hopkins-Hill;Tomas Hudlicky .Explorations of [4+2] and [5+2] Cycloadditions of Dienylcyclopropane Derived Enzymatically from Cyclopropylbenzene[J].Synlett,2011(19):2891-2895.
[8] Wender PA.;Sperandio D. .A new and selective catalyst for the [5+2] cycloaddition of vinylcyclopropanes and alkynes[J].The Journal of Organic Chemistry,1998(13):4164-4165.
[9] Kim S Y;Chung Y K .Rhodium(I)-catalyzed cycloiso-merization of 1, 6-enynes to bicyclo [4.1.0] heptenes[J].The Journal of Organic Chemistry,2010,75(4):1281-1284.
[10] Wender P A;Williams T J .[(Arene)Rh(cod)]+ complexes as catalysts for [5+2] cycloaddition reactions[J].Angew Chem Int Ed,2002,41(23):4550-4553.
[11] Wender PA.;Love JA.;Williams TJ. .Rhodium-catalyzed [5+2] cycloaddition reactions in water[J].Synlett,2003(9):1295-1298.
[12] Fernando J. Gomez;Nahrain E. Kamber;Nicole M. Deschamps .N-Alkoxyimidazolylidene Transition-Metal Complexes: Application to [5+2] and [4+2] Cycloaddition Reactions[J].Organometallics,2007(18):4541-4545.
[13] Jung Kyu Choi;Su Ho Kim;Juyoung Yoon .A PCT-Based,Pyrene-Armed Calix[4]crown Fluoroionophore[J].The Journal of Organic Chemistry,2006(21):8011-8015.
[14] Gilbertson S R;Hoge G S .Rhodium catalyzed intramolecular [4+2] cycloisomerization reactions[J].Tetrahedron Letters,1998,39(15):2075-2078.
[15] Saito A;Ono T;Hanzawa Y .Cationic Rh(I) catalyst in fluorinated alcohol: Mild intramolecular cycloaddition reactions of ester-tethered unsaturated compounds[J].The Journal of Organic Chemistry,2006(17):6437-6443.
[16] Wang Bin .An efficient Rh-catalyst system for the intramolecular [4+2] and [5+2] cycloaddition reactions[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,2000(42):8041-8044.
[17] Wender P A;Lesser A B;Sirois L E .Rhodium dinaphthocyclooctatetraene complexes:synthesis,chara-cterrization and catalytic activity in [5+2] cycloadditions[J].Angewandte Chemie,2012,124(11):2790-2794.
[18] Xu, X.;Liu, P.;Lesser, A.;Sirois, L.E.;Wender, P.A.;Houk, K.N. .Ligand effects on rates and regioselectivities of Rh(I)-catalyzed (5 + 2) cycloadditions: A computational study of cyclooctadiene and dinaphthocyclooctatetraene as ligands[J].Journal of the American Chemical Society,2012(26):11012-11025.
[19] Paul A. Wender;Hisashi Takahashi;Bernhard Witulski .Transition Metal Catalyzed [5 + 2] Cycloadditions of Vinylcyclopropanes and Alkynes: A Homolog of the Diels-Alder Reaction for the Synthesis of Seven-Membered Rings[J].Journal of the American Chemical Society,1995(16):4720-4721.
[20] Ashfeld BL;Miller KA;Smith AJ;Tran K;Martin SF .[Rh(CO)(2)Cl](2)-catalyzed domino reactions involving allylic substitution and subsequent carbocyclization reactions[J].Organic letters,2005(8):1661-1663.
[21] Brandon L. Ashfeld;Kenneth A. Miller;Anna J. Smith .Features and Applications of [Rh(CO)2Cl]2-Catalyzed Alkylations of Unsymmetrical Allylic Substrates[J].The Journal of Organic Chemistry,2007(24):9018-9031.
[22] Wender PA.;Langkopf E.;Love JA.;Husfeld CO. .First studies of the transition metal-catalyzed [5+2] cycloadditions of alkenes and vinylcyclopropanes: Scope and stereochemistry[J].Journal of the American Chemical Society,1998(8):1940-1941.
[23] Wender PA.;Langkopf E.;Love JA.;Pleuss N.;Husfeld CO. .The first metal-catalyzed intramolecular [5+2] cycloadditions of vinylcyclopropanes and alkenes: Scope, stereochemistry, and asymmetric catalysis[J].Tetrahedron,1998(25):7203-7220.
[24] Wang, YY;Wang, JX;Su, JC;Huang, F;Jiao, L;Liang, Y;Yang, D;Zhang, SW;Wender, PA;Yu, ZX .A computationally designed Rh(I)-catalyzed two-component [5+2+1] cycloaddition of ene-vinylcyclopropanes and CO for the synthesis of cyclooctenones[J].Journal of the American Chemical Society,2007(33):10060-10061.
[25] Wender, Paul A.;Glorius, Frank;Husfeld, Craig O.;Langkopf, Elke;Love, Jennifer A. .Transition metal-catalyzed [5+2] cycloadditions of allenes and vinylcyclopropanes: First studies of endo-exo selectivity, chemoselectivity, relative stereochemistry, and chirality transfer[J].Journal of the American Chemical Society,1999(22):5348-0.
[26] Wender P A;Haustedt L O;Lim J et al.Asymmetric catalysis of the [5+2] cycloaddition reaction of vinyl-cyclopropanes and π-systems[J].Journal of the American Chemical Society,2006,128(19):6302-6303.
[27] Inagaki F;Sugikubo K;Miyashita Y et al.Rhodium(I)-catalyzed intramolecular [5+2] cycloaddition reactions of alkynes and allenylcyclopropanes:construction of bicycle [5.4.0] undecatrienes and bicyclo [5.5.0] dodecatrienes[J].Angew Chem Int Ed,2010,49(12):2206-2210.
[28] Jiao L;Ye SY;Yu ZX .Rh(l)-catalyzed Intramolecular [3+2] cycloaddition of trans-vinylcycloproplane-enes[J].Journal of the American Chemical Society,2008(23):7178-7179.
[29] Paul Binger;Petra Wedemann;Sergei I. Kozhushkov;Armin de Meijere .Palladium(0)- and Nickel(0)-Catalyzed [3 + 2] Co-Cyclization Reactions of Bicyclopropylidene with Alkenes[J].European journal of organic chemistry,1998(1):113-119.
[30] Wender PA.;Fuji M.;Rieck H. .The transition metal-catalyzed intermolecular [5+2] cycloaddition: The homologous Diels-Alder reaction[J].Journal of the American Chemical Society,1998(42):10976-10977.
[31] Paul A.Wender;Claudia M.Barzilay;Alaric J.Dyckman .The First Intermolecular Transition Metal-Catalyzed [5+2] Cycloadditions with Simple, Unactivated, Vinylcyclopropanes[J].Journal of the American Chemical Society,2001(1):179-180.
[32] Hermann A. Wegner;Armin de Meijere;Paul A. Wender .Transition Metal-Catalyzed Intermolecular [5+2] and [5+2+1] Cycloadditions of Allenes and Vinylcyclopropanes[J].Journal of the American Chemical Society,2005(18):6530-6531.
[33] Yu Z X;Wender P A;Houk K N .On the mechanism of [Rh(CO)2Cl] 2-catalyzed intermolecular(5+2)reactions between vinylcyclopropanes and alkynes[J].Journal of the American Chemical Society,2004,126(30):9154-9155.
[34] Wender PA;DeChristopher BA;Schrier AJ .Efficient synthetic access to a new family of highly potent bryostatin analogues via a prins-driven macrocyclization strategy[J].Journal of the American Chemical Society,2008(21):6658-6659.
[35] Shu X;Huang S;Shu D et al.Interception of a rautenstrauch intermediate by alkynes for [5+2] cyclo-addition:Rhodium-catalyzed cycloisomerization of 3-acyloxy-4-ene-1,9-diynes to bicyclo [5.3.0] decatrienes[J].Angew Chem Int Ed,2011,50(35):8153-8156.
[36] Shu, X.-Z.;Li, X.;Shu, D.;Huang, S.;Schienebeck, C.M.;Zhou, X.;Robichaux, P.J.;Tang, W. .Rhodium-catalyzed intra- and intermolecular [5 + 2] cycloaddition of 3-acyloxy-1,4-enyne and alkyne with concomitant 1,2-acyloxy migration[J].Journal of the American Chemical Society,2012(11):5211-5221.
[37] Paul A. Wender;Masahiro Fuji;Craig O. Husfeld;Jennifer A. Love .Rhodium-Catalyzed [5 + 2] Cycloadditions of Allenes and Vinylcyclopropanes: Asymmetric Total Synthesis of (+)-Dictamnol[J].Organic letters,1999(1):137-139.
[38] Paul A. Wender;Lei Zhang .Asymmetric Total Synthesis of (+)-Aphanamol I Based on the Transition Metal Catalyzed [5 + 2] Cycloaddition of Allenes and Vinylcyclopropanes[J].Organic letters,2000(15):2323-2326.
[39] Ashfeld B L;Martin S F .Enantioselective syntheses of tremulenediol A and tremulenolide A[J].Organic Letters,2005,7(20):4535-4537.
[40] Ashfeld BL;Martin SF .Enantioselective syntheses of tremulenediol A and tremulenolide A[J].Tetrahedron,2006(45):10497-10506.
[41] Barry M.Trost;Jerome Waser;Arndt Meyer .Total Synthesis of(-)-Pseudolaric Acid B[J].Journal of the American Chemical Society,2007(47):14556-14557.
[42] Barry M. Trost;Jerome Waser;Arndt Meyer .Total Synthesis of (-)-Pseudolaric Acid B[J].Journal of the American Chemical Society,2008(48):16424-16434.
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:
  • 1
    0%
  • 2
    0%
  • 3
    0%
  • 4
    0%
  • 5
    0%