Recent advances in 1,3-dipolar cycloaddition reactions on solid supports

Molecular Diversity

Volumn 9, Issue 1-3, 2005, Pages 187-207

  Harju, Krsi ^a   Yli Kauhaluoma, Jari ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

Author keywords

Combinatorial chemistry; Dipolar compound; Dipolar cycloaddition; Dipolarophile; Heterocyclic compounds; Solid phase synthesis

Indexed keywords

ALKENE; ALKYNE; AZIDE; AZOMETHINE YLIDE; HETEROCYCLIC COMPOUND; IMINE; NITRILE OXIDE; NITRONE; ORGANIC COMPOUND; POLYMER; RESIN;

CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CROSS LINKING; CYCLOADDITION; DIASTEREOISOMER; DIPOLE; ENANTIOMER; HYDROLYSIS; ISOMER; ISOMERIZATION; MOLECULE; PRIORITY JOURNAL; PURIFICATION; RACEMIZATION; REACTION ANALYSIS; REVIEW; SOLID; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SUZUKI REACTION; SYNTHESIS; TECHNIQUE;

CHEMISTRY, ORGANIC; HYDROCARBONS, CYCLIC; INDICATORS AND REAGENTS; MOLECULAR CONFORMATION; ORGANIC CHEMICALS;

EID: 15444369225     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11030-005-1339-1     Document Type: Review

References (68)

1. Padwa, A. 1,3-Dipolar Cycloaddition Chemistry, 2 Vols., Wiley, New York, NY, 1984.
2. Kantorowski, E.J. and Kurth, M.J., Dipolar cycloadditions in solid-phase organic synthesis (SPOS), Mol. Diversity, 2 (1996) 207-216.
3. Hollinshead, S.P., Stereoselective synthesis of highly functionalised pyrrolidines via 1,3-dipolar cycloaddition reactions on a solid support, Tetrahedron Lett., 37 (1996) 9157-9160.
4. Dondas, H.A., Grigg, R., MacLachlan, W.S., MacPherson, D.T., Markandu, J., Sridharan, V. and Suganthan, S., Solid phase sequential 1,3-dipolar cycloaddition-Pictet-Spengler reactions, Tetrahedron Lett., 41 (2000) 967-970.
5. Murphy, M.M., Schullek, J.R., Gordon, E.M. and Gallop, M.A., Combinatorial organic synthesis of highly functionalized pyrrolidines: identification of a potent angiotensin converting enzyme inhibitor from a mercaptoacyl proline library, J. Am. Chem. Soc., 117 (1995) 7029-7030.
6. Barrett, A.G.M., Boffey, R.J., Frederiksen, M.U., Newton, C.G. and Roberts, R.S., Pyrrolidine synthesis on polystyrene supports: Development of a 'one-pot' dipolar cycloaddition strategy, Tetrahedron Lett., 42 (2001) 5579-5581.
7. Hoveyda, H.R. and Hall, D.G., Solid-phase synthesis of cleavable N-arylmaleimides: Applications in 1,3-dipolar cycloaddition and in thiol scavenging, Org. Lett., 3 (2001) 3491-3494.
8. Ganguly, A.K., Seah, N., Popov, V., Wang, C.H., Kuang, R., Saksena, A.K., Pramanik, B.N., Chan, T.M. and McPhail, A.T., Solution- and solid-phase synthesis of enantiomerically pure spiro oxindoles, Tetrahedron Lett., 43 (2002) 8981-8983.
9. Caix-Haumesser, S., Hanna, I., Lallemand, J.-Y. and Peyronel, J.-F., Solid-phase synthesis of functionalized tropane derivatives via 1,3-dipolar cycloaddition, Tetrahedron Lett., 42 (2001) 3721-3723.
10. Fuchi, N., Doi, T., Cao, B., Kahn, M. and Takahashi, T., The solid-phase parallel synthesis of β-strand mimetic templates via 1,3-dipolar cycloaddition with resin-bound vinylsulfone, Synlett, (2002) 285-289.
11. Donohue, A.C., Pallich, S. and McCarthy, T.D., Cycloaddition of nitrile imines to resin-bound enamines: A solid phase synthesis of 1,4-diarylpyrazoles, J. Chem. Soc., Perkin Trans. 1 (2001) 2817-2822.
12. Garanti, L., Molteni, G. and Casati, P., Nitrilimine cycloadditions to MeOPEG-bounded alkenyl dipolarophiles, J. Chem. Soc., Perkin Trans. 1 (2002) 2504-2508.
13. Moore, M. and Norris, P., Dipolar cycloaddition reactions on a soluble polymer-supported dipolarophile: Synthesis of sugar-derived triazoles, Tetrahedron Lett., 39 (1998) 7027-7030.
14. Tornøe, C.W., Christensen, C. and Meldal, M., Peptidotriazoles on solid phase: [1,2,3]-Triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides, J. Org. Chem., 67 (2002) 3057-3064.
15. Kuster, G.J. and Scheeren, H.W., High pressure promoted tandem [4 + 2]/[3 + 2] cycloadditions on the solid phase, Tetrahedron Lett., 39 (1998) 3613-3616.
16. Haap, W.J., Kaiser, D., Walk, T.B. and Jung, G., Solid phase synthesis of diverse isoxazolidines via 1,3-dipolar cycloaddition, Tetrahedron, 54 (1998) 3705-3724.
17. Tan, D.S., Foley, M.A., Shair, M.D. and Schreiber, S.L., Stereoselective synthesis of over two million compounds having structural features both reminiscent of natural products and compatible with miniaturized cell-based assays, J. Am. Chem. Soc., 120 (1998) 8565-8566.
18. Tan, D.S., Foley, M.A., Stockwell, B.R., Shair, M.D. and Schreiber, S.L., Synthesis and preliminary evaluation of a library of polycyclic small molecules for use in chemical genetic assays, J. Am. Chem. Soc., 121 (1999) 9073-9087.
19. Pisaneschi, F., Della Monica, C., Cordero, F.M. and Brandi, A., Solid-phase access to polyhydroxypyrrolizidines by 1,3-dipolar cycloaddition of (S)-3-alkoxypyrroline N-oxide to maleate and crotonate derivatives, Tetrahedron Lett., 43 (2002) 5711-5714.
20. Pisaneschi, F., Cordero, F.M. and Brandi, A., Resin linked dipolarophiles to mask nitrones, Synlett, (2003) 1889-1891.
21. Desimoni, G., Faita, G., Galbiati, A., Pasini, D., Quadrelli, P. and Rancati, F., A soluble polymer-bound Evans chiral auxiliary: Synthesis, characterization and use in cycloaddition reactions, Tetrahedron: Asymmetry, 13 (2002) 333-337.
22. Park, K.-H., Olmstead, M.M. and Kurth, M.J., Diastereoselective solid-phase synthesis of novel hydantoinand isoxazoline-containing heterocycles, J. Org. Chem., 63 (1998) 6579-6585.
23. 3-alkylated hydantoins from solid-phase: Synthesis of novel isoxazoloimidazolidinediones, Tetrahedron Lett., 40 (1999) 5841-5844.
24. Park, K.-H., Ehrler, J., Spoerri, H. and Kurth, M.J., Preparation of a 990-member chemical compound library of hydantoin- and isoxazoline-containing heterocycles using multipin technology, J. Comb. Chem., 3 (2001) 171-176.
25. Park, K.-H., Abbate, E., Najdi, S., Olmstead, M.M. and Kurth, M.J., Solution- and solid-phase synthesis of novel hydantoin and isoxazoline- containing heterocycles, J. Chem. Soc., Chem. Commun., (1998) 1679-1680.
26. Park, K.-H. and Kurth, M.J., Solid-phase synthesis of novel heterocycles containing thiohydantoin and isoxazole rings, J. Org. Chem., 64 (1999), 9297-9300.
27. 2-isoxazolines, Tetrahedron Lett., 39 (1998) 939-942.
28. Faita, G., Paio, A., Quadrelli, P., Rancati, F. and Seneci, P., (4S)-p-Hydroxybenzyl-1,3-oxazolidin-2-one as a solid-supported chiral auxiliary in asymmetric 1,3-dipolar cycloadditions, Tetrahedron Lett., 41 (2000) 1265-1269.
29. Faita, G., Paio, A., Quadrelli, P., Rancati, F. and Seneci, P., Solid supported chiral auxiliaries in asymmetric synthesis. Part 2: Catalysis of 1,3-dipolar cycloadditions by Mg(II) cation, Tetrahedron, 57 (2001) 8313-8322.
30. Hwang, S.H. and Kurth, M.J., Versatile "traceless" sulfone linker for SPOS: Preparation of isoxazolinopyrrole 2-carboxylates, J. Org. Chem., 67 (2002) 6564-6567.
31. Lorsbach, B.A., Bagdanoff, J.T., Miller, R.B. and Kurth, M.J., Isoxazolinoisoquinoline heterocycles via solid-phase Reissert and Suzuki reactions, J. Org. Chem., 63 (1998) 2244-2250.
32. Cheng, W.-C., Wong, M., Olmstead, M.M. and Kurth, M.J., Solid-phase synthesis of novel isoxazolocyclobutanones and isoxazolinocyclobutenones, Org. Lett., 4 (2002) 741-744.
33. Barrett, A.G.M., Procopiou, P.A. and Voigtmann, U., Solid-phase synthesis of isoxazoles using vinyl ethers as chameleon catches, Org. Lett., 3 (2001) 3165-3168.
34. Huang, X. and Xu, W.-M., Use of selenium-bound resin for the solid-phase synthesis of substituted isoxazolyl-substituted (E)-olefins, Org. Lett., 5 (2003) 4649-4652.
35. 3-containing acrylates and 4-isoxazolecarboxylates, J. Fluorine Chem., 111 (2001) 241-246.
36. Makaritis, A., Georgiadis, D., Dive, V. and Yiotakis, A., Diastereoselective solution and multipin-based combinatorial array synthesis of a novel class of potent phosphinic metalloprotease inhibitors, Chem. Eur. J., 9 (2003) 2079-2094.
37. Shang, Y.-J. and Wang, Y.-G., Soluble polymer-supported synthesis of isoxazoles, Tetrahedron Lett., 43 (2002) 2247-2249.
38. Komatsu, M., Okada, H., Akaki, T., Oderaotoshi, Y. and Minakata, S., Generation and cycloaddition of polymer-supported azomethine ylide via a 1,2-silatropic shift of α-silylimines: Traceless synthesis of pyrrolidine derivatives, Org. Lett., 4 (2002) 3505-3508.
39. Okada, H., Akaki, T., Oderaotoshi, Y., Minakata, S. and Komatsu, M., Generation and cycloaddition of polymer-supported azomethine ylide by utilizing the characteristics of silicon: A facile route to pyrrolidines and pyrroles from α-silylimines bound to resin, Tetrahedron, 59 (2003) 197-205.
40. Washizuka, K.-I., Nagai, K., Minakata, S., Ryu, I. and Komatsu, M., Generation and cycloaddition of polymer-supported azomethine imines: Traceless synthesis of pyrazole derivatives from α-silylnitrosoamide derivatives bound to resin, Tetrahedron Lett., 41 (2000) 691-695.
41. Kawamura, Y., Akai, Y. and Tsukayama, M., Combinatorial synthesis of exohedrally modified fullerene derivatives, Int. J. Modern Phys. B, 17 (2003) 1910-1915.
42. Bicknell, A.J., Hird, N.W. and Readshaw, S.A., Efficient robotic synthesis. Multi-component preparation of a tricyclic template by solid phase Tsuge reaction, Tetrahedron Lett., 39 (1998) 5869-5872.
43. Brooking, P., Crawshaw, M., Hird, N.W., Jones, C., MacLachlan, W.S., Readshaw, S.A. and Wilding, S., The development of a solid phase Tsuge reaction and its application in high throughput robotic synthesis, Synthesis, (1999) 1986-1992.
44. Goff, D.A., Combinatorial synthesis of indolizines on solid support, Tetrahedron Lett., 40 (1999), 8741-8745.
45. Strocker, A.M., Keating, T.A., Tempest, P.A. and Armstrong, R.W., Use of a convertible isocyanide for generation of Ugi reaction derivatives on solid support: Synthesis of α-acylaminoesters and pyrroles, Tetrahedron Lett., 37 (1996) 1149-1152.
46. Mjalli, A.M.M., Sarshar, S. and Baiga, T.J., Solid phase synthesis of pyrroles derived from a four component condensation, Tetrahedron Lett., 37 (1996), 2943-2946.
47. Bilodeau, M.T. and Cunningham, A.M., Solid-supported synthesis of imidazoles: A strategy for direct resin-attachment to the imidazole core, J. Org. Chem., 63 (1998) 2800-2801.
48. Gowravaram, M.R. and Gallop, M.A., "Traceless" solid-phase synthesis of furans via 1,3-dipolar cycloaddition reactions of isomünchnones, Tetrahedron Lett., 38 (1997) 6973-6976.
49. Whitehouse, D.L., Nelson, K.H., Jr, Savinov, S.N. and Austin, D.J., A chemoselective rhodium(II) mediated solid phase 1,3-dipolar cycloaddition and its application to a thermally self-cleaving furan scaffold, Tetrahedron Lett., 38 (1997) 7139-7142.
50. Whitehouse, D.L., Nelson, K.H., Jr, Savinov, S.N., Löwe, R.S. and Austin, D.J., A metathetical cycloaddition-cycloreversion approach to the formation of furan scaffold libraries, Bioorg. Med. Chem., 6 (1998) 1273-1282.
51. Savinov, S.N. and Austin, D.J., Diastereofacial solid phase synthesis and self-promoted cleavage of a [2.2.1] bicyclic diversity scaffold, Org. Lett., 4 (2002) 1419-1422.
52. Löber, S., Rodriguez-Loaiza, P. and Gmeiner, P., Click linker: Efficient and high-yielding synthesis of a new family of SPOS resins by 1,3-dipolar cycloaddition, Org. Lett., 5 (2003) 1753-1755.
53. Garanti, L. and Molteni, G., MeOPEG-bounded azide cycloadditions to alkynyl dipolarophiles, Tetrahedron Lett., 44 (2003) 1133-1135.
54. Harju, K., Vahermo, M., Mutikainen, I. and Yli-Kauhaluoma, J., Solid-phase synthesis of 1,2,3-triazoles via 1,3-dipolar cycloaddition, J. Comb. Chem., 5 (2003) 826-833.
55. Kuster, G.J. and Scheeren, H.W., The preparation of resin-bound nitroalkenes and some applications in high pressure promoted cycloadditions, Tetrahedron Lett., 41 (2000) 515-519.
56. Kobayashi, S. and Akiyama, R., Lanthanide triflate-catalyzed 1,3-dipolar cycloaddition reactions of polymer-supported nitrones with alkenes for the preparation of diverse 2-isoxazoline derivatives, Tetrahedron Lett., 39 (1998) 9211-9214.
57. Shankar, B.B., Yang, D.Y., Girton, S. and Ganguly, A.K., One pot solid phase synthesis of isoxazolines, Tetrahedron Lett., 39 (1998) 2447-2448.
58. Zou, N. and Jiang, B., Solid phase asymmetric synthesis of isoxazolines, J. Comb. Chem., 2 (2000) 6-7.
59. Beebe, X., Schore, N.E. and Kurth, M.J., Polymer-supported synthesis of 2,5-disubstituted tetrahydrofurans, J. Am. Chem. Soc., 114 (1992) 10061-10062.
60. Ockey, D.A., Lane, D.R., Seeley, J.A. and Schore, N.E., Synthesis of cyclic ethers utilizing a cyclization-fragmentation strategy, Tetrahedron, 56 (2000) 711-717.
61. Lin, X.-F., Cui, S.-L. and Wang, Y.-G., Rapid one-pot solid-phase synthesis of 1,2,4-oxadiazolines, Chem. Lett., 32 (2003) 842-843.
62. Faita, G., Mella, M., Mortoni, A., Paio, A., Quadrelli, P. and Seneci, P., Solid-supported nitrile oxides as stable and valuable reactive intermediates, Eur. J. Org. Chem., (2002) 1175-1183.
63. Cereda, E., Ezhaya, A., Quai, M. and Barbaglia, W., Solid-phase synthesis of 3-hydroxymethyl isoxazoles via resin bound nitrile oxides, Tetrahedron Lett., 42 (2001) 4951-4953.
64. Marx, M.A., Grillot, A.-L., Louer, C.T., Beaver, K.A. and Bartlett, P.A., Synthetic design for combinatorial chemistry. Solution and polymer-supported synthesis of polycyclic lactams by intramolecular cyclization of azomethine ylides, J. Am. Chem. Soc., 119 (1997) 6153-6167.
65. Gong, Y.-D., Najdi, S., Olmstead, M.M. and Kurth, M.J., Solid-phase synthesis: Intramolecular azomethine ylide cycloaddition (→proline) and carbanilide cyclization (→hydantoin) reactions, J. Org. Chem., 63 (1998) 3081-3086.
66. Peng, G., Sohn, A. and Gallop, M.A., Stereoselective solid-phase synthesis of a triaza tricyclic ring system: A new chemotype for lead discovery, J. Org. Chem., 64 (1999) 8342-8349.
67. Cironi, P., Manzanares, I., Albericio, F. and Álvarez, M., Solid-phase total synthesis of the pentacyclic system lamellarins U and L, Org. Lett., 5 (2003) 2959-2962.
68. Chao, E.Y., Minick, D.J., Sternbach, D.D., Shearer, B.G. and Collins, J.L., A novel method for the generation of nitrile oxides on a solid phase: Application to the synthesis of substituted benzopyranoisoxazoles, Org. Lett., 4 (2002) 323-326.