Catalytic, asymmetric vinylogous Mukaiyama aldol reactions of pyrrole- and furan-based dienoxy silanes: How the diene heteroatom impacts stereocontrol

Advanced Synthesis and Catalysis

Volumn 352, Issue 11-12, 2010, Pages 2011-2022

  Curti, Claudio ^a   Ranieri, Beatrice ^a   Battistini, Lucia ^a   Rassu, Gloria ^b   Zambrano, Vincenzo ^a   Pelosi, Giorgio ^a   Casiraghi, Giovanni ^a   Zanardi, Franca ^a  

^a UNIVERSITY OF PARMA   (Italy)

^b CNR   (Italy)

Author keywords

Asymmetric catalysis; Asymmetric synthesis; Diastereoselectivity; Enantioselectivity; Heterocyclic dienoxy silanes; Vinylogous aldol reaction

Indexed keywords

EID: 77956359272     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000189     Document Type: Article

References (83)

1. a) G. Casiraghi, F. Zanardi, L. Battistini, G. Rassu, Synlett 2009, 1525-1542
2. b) T. Brodmann, M. Lorenz, R. Schackel, S. Simsek, M. Kalesse, Synlett 2009, 174-192
3. c) S. Hosokawa, K. Tatsuta, Mini-Rev. Org. Chem. 2008, 5, 1-18
4. d) M. Kalesse, J. Hassfeld, in: Asymmetric Synthesis, (Eds.: M. Christmann, S. Braese), Wiley- VCH, Weinheim, 2007, pp 105 - 109
5. e) S. E. Denmark, J. R., Jr. Heemstra, G. L. Beutner, Angew. Chem. 2005, 117, 4760-4777
6. a)Angew. Chem. Int. Ed. 2005, 44, 4682-4698
7. f) M. Kalesse, Top. Curr. Chem. 2005, 244, 43-76
8. g) A. Soriente, M. De Rosa, R. Villano, A. Scettri, Curr. Org. Chem. 2004, 8, 993-1007
9. h) G. Casiraghi, F. Zanardi, G. Appendino, G. Rassu, Chem. Rev. 2000, 100, 1929-1972.
10. For selected, recent examples, see: a) V. Zambrano, G. Rassu, A. Roggio, L. Pinna, F. Zanardi, C. Curti, G. Casiraghi, L. Battistini, Org. Biomol. Chem. 2010, 8, 1725-1730
11. b) F. Zanardi, C. Curti, A. Sartori, G. Rassu, A. Roggio, L. Battistini, P. Burreddu, L. Pinna, G. Pelosi, G. Casiraghi, Eur. J. Org. Chem. 2008, 2273-2287
12. c) C. Curti, F. Zanardi, L. Battistini, A. Sartori, G. Rassu, L. Auzzas, A. Roggio, L. Pinna, G. Casiraghi, J. Org. Chem. 2006, 71, 225-230
13. d) L. Battistini, C. Curti, F. Zanardi, G. Rassu, L. Auzzas, G. Casiraghi, J. Org. Chem. 2004, 69, 2611-2613
14. e) G. Rassu, L. Auzzas, V. Zambrano, P. Burreddu, L. Pinna, L. Battistini, F. Zanardi, G. Casiraghi, J. Org. Chem. 2004, 69, 1625-1628
15. f) F. Zanardi, L. Battistini, L. Marzocchi, D. Acquotti, G. Rassu, L. Pinna, L. Auzzas, V. Zambrano, G. Casiraghi, Eur. J. Org. Chem. 2002, 1956-1964
16. g) G. Rassu, L. Auzzas, L. Pinna, V. Zambrano, L. Battistini, F. Zanardi, L. Marzocchi, D. Acquotti, G. Casiraghi, J. Org. Chem. 2001, 66, 8070-8075
17. h) F. Zanardi, L. Battistini, G. Rassu, L. Auzzas, L. Pinna, L. Marzocchi, D. Acquotti, G. Casiraghi, J. Org. Chem. 2000, 65, 2048-2064.
18. See also i) S. Gao, Q. Wang, L. J.-S. Huang, L. Lum, C. Chen, J. Am. Chem. Soc. 2010, 132, 371-383
19. j) M. Frings, I. Atodiresei, J. Runsink, G. Raabe, C. Bolm, Chem. Eur. J. 2009, 15, 1566-1569
20. k) K. Kong, D. Romo, C. Lee, Angew. Chem. 2009, 121, 7538-7541
21. a)Angew. Chem. Int. Ed. 2009, 48, 7402-7405
22. l) D. A. Evans, L. Kværnø, T. B. Dunn, A. Beauchemin, B. Raymer, J. A. Mulder, E. J. Olhava, M. Juhl, K. Kagechika, D. A. Favor, J. Am. Chem. Soc. 2008, 130, 16295-16309
23. m) R. K., Jr. Boeckman, J. E. Pero, D. J. Boehmler, J. Am. Chem. Soc. 2006, 128, 11032-11033.
24. Preliminary communication of part of this work: C. Curti, A. Sartori, L. Battistini, G. Rassu, F. Zanardi, G. Casiraghi, Tetrahedron Lett. 2009, 50, 3428-3431.
25. a) S. E. Denmark, Chimia 2008, 62, 37-40
26. b)S.E. Denmark, J. R., Jr. Heemstra, Org. Lett. 2003, 5, 2303-2306
27. c) S. E. Denmark, T. Wynn, G. L. Beutner, J. Am. Chem. Soc. 2002, 124, 13405-13407.
28. a) S. E. Denmark, J. R. Heemstra Jr. , J. Org. Chem. 2007, 72, 5668-5688
29. b) S. E. Denmark, J. R. Heemstra Jr. , J. Am. Chem. Soc. 2006, 128, 1038-1039
30. c) S. E. Denmark, G. L. Beutner, T. Wynn, M. D. Eastgate, J. Am. Chem. Soc. 2005, 127, 3774-3789
31. d) S. E. Denmark, S. Fujimori, J. Am. Chem. Soc. 2005, 127, 8971-8973
32. e) S. E. Denmark, J. R. Heemstra Jr. , Synlett 2004, 2411-2416
33. f) S. E. Denmark, G. L. Beutner, J. Am. Chem. Soc. 2003, 125, 7800-7801.
34. See also g) L. Palombi, M. R. Acocella, N. Celenta, A. Massa, R. Villano, A. Scettri, Tetrahedron: Asymmetry 2006, 17, 3300-3303
35. h) R. Villano, M. R. Acocella, A. Massa, L. Palombi, A. Scettri, Tetrahedron: Asymmetry 2006, 17, 3332-3334.
36. For clever applications of OXB-promoted asymmetric VMAR, see: a) S. Simsek, M. Kalesse, Tetrahedron Lett. 2009, 50, 3485-3488
37. b) A. B. Smith III, J. A. Jurica, S. P. Walsh, Org. Lett. 2008, 10, 5625-5628
38. c) S. Simsek, M. Horzella, M. Kalesse, Org. Lett. 2007, 9, 5637-5639
39. d) S.-I. Kiyooka, M. A. Hena, T. Yabukami, K. Murai, F. Goto, Tetrahedron Lett. 2000, 41, 7511-7516
40. e) S.-I. Kiyooka, M. A. Hena, J. Org. Chem. 1999, 64, 5511-5523.
41. a) M. Szlosek, B. Figadère Angew. Chem. 2000, 112, 1869-1871
42. a)Angew. Chem. Int. Ed. 2000, 39, 1799-1801
43. b) K. Mikami, S. Matsukawa, T. Volk, M. Terada, Angew. Chem. 1997, 109, 2936-2939
44. a)Angew. Chem. Int. Ed. Engl. 1997, 36, 2768-2771.
45. See also c) L. V. Heumann, G. E. Keck, Org. Lett. 2007, 9, 4275-4278
46. d) I. Paterson, A. D. Findlay, G. J. Florence, Org. Lett. 2006, 8, 2131-2134
47. e) I. Paterson, G. J. Florence, A. C. Heimann, A. C. Mackay, Angew. Chem. 2005, 117, 1154-1157
48. a)Angew. Chem. Int. Ed. 2005, 44, 1130-1133
49. f) R. Villano, M. R. Acocella, M. De Rosa, M. A. Soriente, A. Scettri, Tetrahedron: Asymmetry 2004, 15, 2421-2424
50. g) M. De Rosa, M. R. Acocella, M. F. Rega, A. Scettri, Tetrahedron: Asymmetry 2004, 15, 3029-3033
51. h) M. De Rosa, M. R. Acocella, R. Villano, A. Soriente, A. Scettri, Tetrahedron: Asymmetry 2003, 14, 2499-2502
52. i) I. Paterson, R. D. M. Davies, A. C. Heimann, R. Marquez, A Meyer, Org. Lett. 2003, 5, 4477-4480
53. j) M. Szlosek, X. Franck, B. Figadère, A. Cavé, J. Org. Chem. 1998, 63, 5169-5172
54. k) M. Sato, S. Sunami, Y. Sugita, C. Kaneko, Heterocycles 1995, 41, 1435-1444.
55. For clever applications of copper-bisoxazoline-catalyzed asymmetric VMAR, see: a) A. Landa, B. Richter, R. L. Johansen, A. Minkkil, K. A. Jørgensen, J. Org. Chem. 2007, 72, 240-245
56. b) J. C.-D. Le, B. L. Pagenkopf, Org. Lett. 2004, 6, 4097-4099
57. c) D. A. Evans, E. Hu, J. D. Burch, G. Jaeschke, J. Am. Chem. Soc. 2002, 124, 5654-5655
58. d) D. A. Evans, D. M. Fitch, T. E. Smith, V. J. Cee, J. Am. Chem. Soc. 2000, 122, 10033-10046
59. e) D. A. Evans, M. C. Kozlowski, J. A. Murry, C. S. Burgey, K. R. Campos, B. T. Connell, R. J. Staples, J. Am. Chem. Soc. 1999, 121, 669-685
60. f) D. A. Evans, C. S. Burgey, M. C. Kozlowski, S. W. Tregay, J. Am. Chem. Soc. 1999, 121, 686-699
61. g) D. A. Evans, P. H. Carter, E. M. Carreira, A. B. Charette, J. A. Prunet, M. Lautens, J. Am. Chem. Soc. 1999, 121, 7540-7552
62. h) D. A. Evans, J. A. Murry, M. C. Kozlowski, J. Am. Chem. Soc. 1996, 118, 5814-5815.
63. During silica gel chromatographic purification, N-Bn-, N-PMB-, and N-allyl-protected unsaturated lactams proved rather unstable due to silica gel-triggered conversion to the corresponding alkylidene products.
64. In the present VMAR procedure, N-alkyl-substituted pyrroles 1h, 1i, and 1j proved more reactive than their N-acyl counterparts, requiring the reactions to be executed at shorter reaction times. As pinpointed by Denmark (ref.[5a]), a correlation between nucleophilicity of the γ-carbon site of the donor component and enantioselectivity of the products may be done, based on the 13C NMR chemical shift of the g-carbons of the dienolate species. That is, the more downfield the Cγ chemical shift, the less nucleophilic and reactive is the carbon site, and the more enantioselective is the subsequent VMAR. This trend was actually observed for the series of the vinylogous donors in this work (see the Supporting Information for details).
65. a) D. A. Evans, L. Kværnø, T. B. Dunn, A. Beauchemin, B. Raymer, J. A. Mulder, E. J. Olhava, M. Juhl, K. Kagechika, D. A. Favor, J. Am. Chem. Soc. 2008, 130, 16295-16309
66. b) S. Onitsuka, Y. Matsuoka, R. Irie, T. Katuski, Chem. Lett. 2003, 32, 974-975.
67. Conditions optimized during a previous work employing similar furan-based reagents in direct VMARs. See: C. Curti, A. Sartori, L. Battistini, G. Rassu, P. Burreddu, F. Zanardi, G. Casiraghi, J. Org. Chem. 2008, 73, 5446-5451.
68. a) M. De Rosa, C. Talotta, A. Soriente, Lett. Org. Chem. 2009, 6, 301-305
69. b) M. Bella, G. Piancatelli, A. Squarcia, C. Trolli, Tetrahedron Lett. 2000, 41, 3669-3672
70. c) H. Uno, Y. Nishihara, N. Mizobe, N. Ono, Bull. Chem. Soc. Jpn. 1999, 72, 1533-1539
71. d) I. Baussanne, J. Royer, Tetrahedron Lett. 1996, 37, 1213 - 1216;
72. e) R. Rico, F. Bermejo, Tetrahedron Lett. 1996, 37, 5809-5812.
73. G. Casiraghi, L. Colombo, G. Rassu, P. Spanu, G. Gasparri Fava, M. Ferrari Belicchi, Tetrahedron 1990, 46, 5807-5824.
74. a) J. Gawroński, K. Gawroń ska, M. Kwit, K. Kacprzak, U. Rychlewska, Chirality 2004, 16, 405-413
75. b) A. D. Cuiper, M. Brzostowska, J. K. Gawroń ski, W. J. J. Smeets, A. L. Spek, H. Hiemstra, R. M. Kellogg, B. L. Feringa, J. Org. Chem. 1999, 64, 2567-2570
76. c) J. K. Gawroń ski, Q. H. Chen, Z. Geng, B. Huang, M. R. Martin, A. I. Mateo, M. Brzostowska, U. Rychlewska, B. L. Feringa, Chirality 1997, 9, 537-544
77. d) J. K. Gawro ński, A. van Oeveren, H. van der Deen, C. W. Leung, B. L. Feringa, J. Org. Chem. 1996, 61, 1513-1515
78. e) I. Uchida, K. Kuriyama, Tetrahedron Lett. 1974, 3761-3764.
79. See also ref.[2j] Heteroaromatic compounds syn-3ea and syn-3fa are (5S,1'R)-configured, due to nominal change of the C1' absolute configuration according to the Cahn-Ingold- Prelog priority rules.
80. Several publications exist dealing with racemic and asymmetric syntheses of aromatic butenolides of type 6. As we searched through the reported data, we found that all relative syn/anti configurational assignments were consistent (complete matching of 1H and13C NMR parameters), whereas the absolute configurations were not. So, to the best of our knowledge, this is the first report that unambiguously clarifies this point. See, for example, refs.[5h,7a,7j] See also: a) G. Cafeo, M. De Rosa, F. Kohnke, A. Soriente, C. Talotta, L. Valenti, Molecules 2009, 14, 2594-2601
81. b) M. De Rosa, L. Citro, A. Soriente, Tetrahedron Lett. 2006, 47, 8507-8510
82. c) M. Acocella, M. De Rosa, A. Massa, L. Palombi, R. Villano, A. Scettri, Tetrahedron 2005, 61, 4091-4097.
83. In the present VMAR processes, a generalized catalytic cycle may apply, as recently postulated and experimentally supported by Denmark. See: S. E. Denmark, B. M. Eklov, P. J. Yao, M. D. Eastgate, J. Am. Chem. Soc. 2009, 131, 11770-11787.