PdII-catalyzed spiroketalization of ketoallylic diols

Chemistry - A European Journal

Volumn 19, Issue 35, 2013, Pages 11613-11621

  Palmes, Jean A ^a   Paioti, Paulo H S ^a   De Souza, Leonardo Perez ^a   Aponick, Aaron ^a  

^a University of Florida   (United States)

Author keywords

anomeric effect; catalysis; ketoallylic diols; palladium; spiroketalization

Indexed keywords

ALLYLIC ALCOHOL; ANOMERIC EFFECT; CHIRAL INFORMATION; CYCLIZATION REACTIONS; KETOALLYLIC DIOLS; SPIROKETALIZATION; STEREOCHEMICAL CONTROL; STEREOSELECTIVE METHOD;

CHAINS; CYCLIZATION; PALLADIUM; STEREOSELECTIVITY;

CATALYSIS;

FURAN DERIVATIVE; PALLADIUM; PALLADIUM CHLORIDE; SPIRO COMPOUND; SPIROKETAL;

ANOMERIC EFFECT; ARTICLE; CATALYSIS; CHEMISTRY; KETOALLYLIC DIOLS; SPIROKETALIZATION; STEREOISOMERISM;

ANOMERIC EFFECT; CATALYSIS; KETOALLYLIC DIOLS; PALLADIUM; SPIROKETALIZATION;

CATALYSIS; FURANS; PALLADIUM; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 84882921916     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201301723     Document Type: Article

References (92)

1. D. O'Hagan, The Polyketide Metabolites, Ellis Horwood, Chichester, 1991
2. D. O'Hagan, Nat. Prod. Rep. 1995, 12, 1
3. R. D. Norcross, I. Paterson, Chem. Rev. 1995, 95, 2041
4. M. T. Fletcher, W. Kitching, Chem. Rev. 1995, 95, 789
5. S. Favre, P. Vogel, S. Gerber-Lemaire, Molecules 2008, 13, 2570.
6. G. R. Pettit, Z. A. Cichacz, F. Gao, C. L. Herald, M. R. Boyd, J. M. Schmidt, J. N. A. Hooper, J. Org. Chem. 1993, 58, 1302
7. G. R. Pettit, Z. A. Cichacz, F. Gao, C. L. Herald, M. R. Boyd, J. Chem. Soc. Chem. Commun. 1993, 1166
8. M. Kobayashi, S. Aoki, H. Sakai, K. Kawazoe, N. Kihara, T. Sasaki, I. Kitagawa, Tetrahedron Lett. 1993, 34, 2795
9. M. Kobayashi, S. Aoki, H. Sakai, N. Kihara, T. Sasaki, I. Kitagawa, Chem. Pharm. Bull. 1993, 41, 989
10. M. Kobayashi, S. Aoki, I. Kitagawa, Tetrahedron Lett. 1994, 35, 1243
11. M. Kobayashi, S. Aoki, K. Gato, I. Kitagawa, Chem. Pharm. Bull. 1996, 44, 2142
12. N. Fusetani, K. Shinoda, S. Matsunaga, J. Am. Chem. Soc. 1993, 115, 3977.
13. D. Gouiffès, S. Moreau, N. Helbecque, J. L. Bernier, J. P. Hénichart, Y. Barbin, D. Laurent, J. F. Verbist, Tetrahedron 1988, 44, 451
14. J. F. Biard, C. Roussakis, J. M. Kornprobst, D. Gouiffes-Barbin, J. F. Verbist, P. Cotelle, M. P. Foster, C. M. Ireland, C. Debitus, J. Nat. Prod. 1994, 57, 1336.
15. D. Uemura, K. Takahashi, T. Yamamoto, C. Katayama, J. Tanaka, Y. Okumura, Y. Hirata, J. Am. Chem. Soc. 1985, 107, 4796
16. G. R. Pettit, R. Tan, F. Gao, M. D. William, D. L. Doubek, M. R. Boyd, J. M. Schmidt, J.-C. Chapuis, E. Hamel, R. Bai, J. N. A. Hooper, L. P. Tackett, J. Org. Chem. 1993, 58, 2538
17. M. Litaudon, J. B. Hart, J. W. Blunt, R. J. Lake, M. H. G. Munro, Tetrahedron Lett. 1994, 35, 9435
18. M. Litaudon, S. J. H. Hickford, R. E. Lill, R. J. Lake, J. W. Blunt, M. H. G. Munro, J. Org. Chem. 1997, 62, 1868
19. G. R. Pettit, C. L. Herald, M. R. Boyd, J. E. Leet, C. Dufresne, D. L. Doubek, J. M. Schmidt, R. L. Cerny, J. N. A. Hooper, K. C. Rutzler, J. Med. Chem. 1991, 34, 3339
20. G. R. Pettit, F. Gao, D. L. Doubek, M. R. Boyd, E. Hamel, R. Bai, J. M. Schmidt, L. P. Tackett, K. Rutzler, Gazz. Chim. Ital. 1993, 123, 371
21. G. R. Pettit, Y. Ichihara, G. Wurzel, M. D. Williams, J. M. Schmidt, J.-C. Chapuis, J. Chem. Soc. Chem. Commun. 1995, 3, 383.
22. L.-G. Milroy, G. Zinzalla, F. Loiseau, Z. Qian, G. Prencipe, C. Pepper, C. Fegan, S. V. Ley, ChemMedChem 2008, 3, 1922.
23. F. Perron, K. F. Albizati, Chem. Rev. 1989, 89, 1617
24. J. E. Aho, P. M. Pihko, T. K. Rissa, Chem. Rev. 2005, 105, 4406
25. K. T. Mead, B. N. Brewer, Curr. Org. Chem. 2003, 7, 227
26. B. Rama Raju, A. K. Saikia, Molecules 2008, 13, 1942
27. S. V. Ley, L.-G. Milroy, R. M. Myers, "Product Class 9: Spiroketals". Science of Synthesis 2007, 29, 613
28. R. G. Carter, D. L. Kuiper, "Asymmetric Synthesis of Spiroketals, Bisspiroketals and Spiroaminals" in Stereoselective Synthesis 2 Stereoselective Reactions of Carbonyl and Imino Groups (Ed.: G. A. Molander), Thieme, 2010, pp. 863-914
29. J. Palmes, A. Aponick, Synthesis 2012, 3699
30. M. Rudolph, A. S. K. Hashmi, Chem. Soc. Rev. 2012, 41, 2448.
31. S. Mitsuhashi, H. Shima, T. Kawamura, K. Kikuchi, M. Oikawa, A. Ichihara, H. Oikawa, Bioorg. Med. Chem. Lett. 1999, 9, 2007
32. F. M. Uckun, C. Mao, A. O. Vassilev, H. Huang, S.-T. Jan, Bioorg. Med. Chem. Lett. 2000, 10, 541
33. H. Huang, C. Mao, S.-T. Jan, F. M. Uckun, Tetrahedron Lett. 2000, 41, 1699.
34. P. Deslongchamps, D. D. Rowan, N. Pothier, T. Sauve, J. K. Saunders, Can. J. Chem. 1981, 59, 1105. For extensive reviews on stereoelectronic effects, see
35. A. J. Kirby, The anomeric effect and related stereoelectronic effects at oxygen, Springer, New York, 1983
36. P. Deslongchamps, Stereoelectronic effects in organic chemistry, Pergamon Press, Oxford, 1983
37. G. R. J. Thatcher, The Anomeric Effect and Associated Stereoelectronic Effects, ACS Symposium Series 539, American Chemical Society, Washington, DC, 1985
38. E. Juaristi; G. Cuevas, The Anomeric Effect, CRC Press, Boca Raton, FL, 1995.
39. For recent examples, see
40. B. Liu, J. K. De Brabander, Org. Lett. 2006, 8, 4907
41. B. D. Sherry, L. Maus, B. N. Laforteza, F. D. Toste, J. Am. Chem. Soc. 2006, 128, 8132
42. S. B. Moilanen, J. S. Potuzak, D. S. Tan, J. Am. Chem. Soc. 2006, 128, 1792
43. D. Vellucci, S. D. Rychnovsky, Org. Lett. 2007, 9, 711
44. J. Matsuo, S. Sasaki, H. Tanaka, H. Ishibashi, J. Am. Chem. Soc. 2008, 130, 11600
45. M. Lejkowski, P. Banerjee, J. Runsink, H.-J. Gais, Org. Lett. 2008, 10, 2713
46. L.-Z. Dai, M. Shi, Chem. Eur. J. 2008, 14, 7011
47. A. Aponick, C.-Y. Li, J. A. Palmes, Org. Lett. 2009, 11, 121
48. J. Mandel, N. Dubois, M. Neuburger, N. Blanchard, Chem. Commun. 2011, 47, 10284
49. Y. Xie, P. Floreanceig, Chem. Sci. 2011, 2, 2423
50. K. Ravindar, M. Sridhar Reddy, P. Deslongchamps, Org. Lett. 2011, 13, 3178
51. J. M. Wurst, G. Liu, D. S. Tan, J. Am. Chem. Soc. 2011, 133, 7916
52. I. Coric, B. List, Nature 2012, 483, 315
53. Z. Sun, G. A. Winschel, A. Borovika, P. Nagorny, J. Am. Chem. Soc. 2012, 134, 8074
54. I. Volchkov, K. Sharma, E. J. Cho, D. Lee, Chem. Asian J. 2011, 6, 1961.
55. A. Guérinot, A. Serra-Muns, C. Gnamm, C. Bensoussan, S. Reymond, J. Cossy, Org. Lett. 2010, 12, 1808
56. M. Commandeur, C. Commandeur, J. Cossy, Org. Lett. 2011, 13, 6018.
57. A. Aponick, C.-Y. Li, B. Biannic, Org. Lett. 2008, 10, 669
58. A. Aponick, B. Biannic, Synthesis 2008, 3356
59. A. Aponick, C. Y. Li, J. Malinge, E. Finco Marques, Org. Lett. 2009, 11, 4624
60. A. Aponick, B. Biannic, M. R. Jong, Chem. Commun. 2010, 46, 6849
61. B. Biannic, A. Aponick, Eur. J. Org. Chem. 2011, 6605
62. T. Ghebreghiorgis, B. Biannic, B. H. Kirk, D. H. Ess, A. Aponick, J. Am. Chem. Soc. 2012, 134, 16307
63. A. Aponick, B. Biannic, Org. Lett. 2011, 13, 1330.
64. J. Uenishi, M. Ohmi, A. Ueda, Tetrahedron Lett. 2005, 46, 1299
65. N. Kawai, J.-M. Lagrange, M. Ohmi, J. Uenishi, J. Org. Chem. 2006, 71, 4530
66. N. Kawai, J.-M. Lagrange, J. Uenishi, Eur. J. Org. Chem. 2007, 2808
67. J. Uenishi, Y. S. Vikhe, N. Kawai, Chem. Asian J. 2008, 3, 473
68. Y. S. Vikhe, S. M. Hande, N. Kawai, J. Uenishi, J. Org. Chem. 2009, 74, 5174
69. H. Yokoyama, K. Otaya, H. Kobayashi, M. Miyazawa, S. Yamaguchi, Y. Hirai, Org. Lett. 2000, 2, 2427 and references cited therein.
70. B. Biannic, A. Aponick, Eur. J. Org. Chem. 2011, 6605
71. N. T. Patil, Chem. Asian J. 2012, 7, 2186
72. J. Muzart, Tetrahedron 2008, 64, 5815
73. M. Bandini, G. Cera, M. Chiarucci, Synthesis 2012, 504
74. J. M. Ketcham, A. Aponick In, Topics in Heterocyclic Chemistry, Vol. 32 (Ed.:, J. Wolfe,), Springer, Berlin, 2013.
75. A. S. K. Hashmi, Angew. Chem. 1995, 107, 1749
76. Angew. Chem. Int. Ed. Engl. 1995, 34, 1581
77. A. S. K. Hashmi, T. L. Ruppert, T. Knofel, J. W. Bats, J. Org. Chem. 1997, 62, 7295
78. A. S. K. Hashmi, L. Schwarz, J. Bats, J. Prakt. Chem. 2000, 342, 40
79. A. S. K. Hashmi, L. Schwarz, J.-H. Choi, T. M. Frost, Angew. Chem. 2000, 112, 2382
80. Angew. Chem. Int. Ed. 2000, 39, 2285.
81. J. E. Whiting, J. T. Edward, Can. J. Chem. 1971, 49, 3799.
82. A. Fürstner, P. W. Davies, Angew. Chem. 2007, 119, 3478
83. Angew. Chem. Int. Ed. 2007, 46, 3410.
84. A. K. Chatterjee, T.-L. Choi, D. P. Sanders, R. H. Grubbs, J. Am. Chem. Soc. 2003, 125, 11360
85. J. Uenishi, Y. Fujikura, N. Kawai, Org. Lett. 2011, 13, 2350.
86. S. D. Zanatta, J. M. White, M. A. Rizzacasa, Org. Lett. 2004, 6, 1041
87. N. Pothier, S. Goldstein, P. Deslongchamps, Helv. Chim. Acta 1992, 75, 604
88. J. Doubský, D. Šaman, J. Zedník, S. VaŠíčková, B. Koutek, Tetrahedron Lett. 2005, 46, 7923
89. L. G. de Oliveira, L. C. Dias, H. Sakauchi, H. Kiyota, Tetrahedron Lett. 2006, 47, 2413
90. W. Kitching, J. A. Lewis, M. V. Perkins, R. Drew, C. J. Moore, V. Schurig, W. A. König, W. Francke, J. Org. Chem. 1989, 54, 3893
91. W. Francke, W. Reith, V. Sinnwell, Chem. Ber. 1980, 113, 2686.
92. R. W. Hoffmann, Chem. Rev. 1989, 89, 1841.