Synthesis of acylsilanes via nickel-catalyzed reactions of α-hydroxyallylsilanes

Organic Letters

Volumn 15, Issue 7, 2013, Pages 1524-1527

  Reddy, Gangireddy PavanKumar ^a   Reddy, J Satyanarayana ^a,b   Das, Saibal ^b   Roisnel, Thierry ^a   Yadav, Jhillu S ^b   Chandrasekhar, Srivari ^b   Grée, René ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

^b INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84875915427     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol4003064     Document Type: Article

References (51)

1. Patrocinio, A. F.; Moran, P. J. S. J. Braz. Chem. Soc. 2001, 12, 7
2. Page, P. C. B.; McKenzie, M. J. Product Subclass 25: Acylsilanes. In Science of Synthesis; Fleming, I., Ed.; Thieme: Stuttgart, 2001; Vol. 4, pp 513-568.
3. Garrett, M. N.; Johnson, J. S. Product Subclass 4: Silicon compound. In Science of Synthesis; Fleming, I., Ed.; Thieme: Stuttgart, Knowledge update 2012/2; Vol. 4, pp 1-85 and references cited therein.
4. A recent Perspective paper on some acylsilanes: Boyce, G. R.; Grezler, S. N.; Johnson, J. S.; Linghu, X.; Malinovski, J. T.; Nicewicz, D. A.; Satterfield, A. D.; Schmitt, D. C.; Steward, K. M. J. Org. Chem. 2012, 77, 4503
5. Brook, A. G. J. Am. Chem. Soc. 1958, 80, 1886
6. Brook, A. G. Acc. Chem. Res. 1974, 7, 77
7. Moser, W. H. Tetrahedron 2001, 57, 2065 and references cited therein
8. Linghu, X.; Bausch, C. C.; Johnson, J. S. J. Am. Chem. Soc. 2005, 127, 1833
9. Tarr, J. C.; Johnson, J. S. J. Org. Chem. 2010, 75, 3317
10. Mattson, A. E.; Bharadwaj, A. R.; Zuhl, A. M.; Scheidt, K. A. J. Org. Chem. 2006, 71, 5715
11. Takeda, K.; Tanaka, T. Synlett 1999, 705
12. Nahm, M. R.; Potnick, J. R.; White, P. S.; Johnson, J. S. J. Am. Chem. Soc. 2006, 128, 2751
13. Garrett, M. R.; Tarr, J. C.; Johnson, J. S. J. Am. Chem. Soc. 2007, 129, 12944
14. Li, F.-Q.; Zhong, S.; Lu, G.; Chan, A. S. C. Adv. Synth. Catal. 2009, 351, 1955
15. Lettan, R. B., II; Reynolds, T. E.; Galliford, C. V.; Scheidt, K. A. J. Am. Chem. Soc. 2006, 128, 15566 and references cited therein
16. Obora, Y.; Ogawa, Y.; Imai, Y.; Kawamura, T.; Tsuji, Y. J. Am. Chem. Soc. 2001, 123, 10489
17. Chen, J.-P.; Ding, C.-H.; Liu, X.-L.; Dai, L.-X. J. Am. Chem. Soc. 2010, 132, 15493
18. Schmink, J. R.; Krska, S. W. J. Am. Chem. Soc. 2011, 133, 19574
19. Ito, K.; Tamashima, H.; Iwasawa, N.; Kusama, H. J. Am. Chem. Soc. 2011, 133, 3716
20. Miller, J. A.; Zweifel, G. Synthesis 1981, 288
21. Miller, J. A.; Zweifel, G. J. Am. Chem. Soc. 1981, 103, 6217
22. Brook, A. G.; Duff, J. M.; Jones, P. F.; Davis, N. R. J. Am. Chem. Soc. 1967, 89, 431
23. Corey, E. J.; Seebach, D.; Freedman, R. J. Am. Chem. Soc. 1967, 89, 434
24. Katritzky, A. R.; Lang, H. J. Org. Chem. 1995, 60, 7612
25. Katritzky, A. R.; Wang, Z.; Lang, H. J. Org. Chem. 1996, 61, 7551
26. Cherkaoui, H.; Soufiaoui, M.; Grée, R. Tetrahedron 2001, 57, 2379
27. Uma, R.; Davies, M. K.; Crevisy, C.; Grée, R. Eur. J. Org. Chem. 2001, 3141
28. Branchadell, V.; Crevisy, C.; Grée, R. Chem.-Eur. J. 2003, 9, 2062
29. Crevisy, C.; Wietrich, M.; Le Boulaire, V.; Uma, R.; Grée, R. Tetrahedron Lett. 2001, 42, 395
30. Cuperly, D.; Petrignet, J.; Crévisy, C.; Grée, R. Chem.-Eur. J. 2006, 12, 3261
31. Petrignet, J.; Prathap, I.; Chandrasekhar, S.; Yadav, J. S.; Grée, R. Angew. Chem., Int. Ed. 2007, 46, 6297
32. Cao, H. T.; Roisnel, T.; Valleix, A.; Grée, R. Eur. J. Org. Chem. 2011, 3430 and references cited therein
33. Danheiser, R. L.; Fink, D. M.; Okano, K.; Tsai, Y.-M.; Szczepanski, S. W. J. Org. Chem. 1985, 50, 5393
34. Buynak, J. D.; Strickland, J. B.; Lamb, G. W.; Khasnis, D.; Modi, S.; Williams, D.; Zhang, H. J. Org. Chem. 1991, 56, 7076
35. Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360
36. Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900
37. Hoveyda, A. H.; Gillingham, D. G.; Van Veldhuizen, J. J.; Kataoka, O.; Garber, S. B.; Kingsbury, J. S.; Harrity, J. P. A. Org. Biomol. Chem. 2004, 2, 8
38. Grubbs, R. H. Adv. Synth. Catal. 2007, 349, 34
39. van der Drift, R. C.; Bouwman, E.; Drent, E. J. Organomet. Chem. 2002, 650, 1
40. Uma, R.; Crevisy, C.; Grée, R. Chem. Rev. 2003, 103, 27
41. Cadierno, V.; Crochet, P.; Gimeno, J. Synlett 2008, 1105 and references cited therein
42. Reactions of acyl silane enolates: Schinzer, D. Synthesis 1989, 179
43. Tandem aldol-Tishchenko reactions: Honda, M.; Iwamoto, R.; Nogami, Y.; Segi, M. Chem. Lett. 2005, 34, 466
44. Mukaiyama-aldol reactions: Honda, M.; Oguchi, W.; Segi, M.; Nakajima, T. Tetrahedron 2002, 58, 6815
45. 3B mediated reactions: Horiuchi, Y.; Taniguchi, M.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1995, 36, 5353
46. CCDC 912880 (3i) and CCDC 912881 (15i) contain the supplementary crystallographic data for this paper, which can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/ cif and are included in the SI.
47. Walkup, R. D.; Kane, R. R.; Boatman, P. D., Jr; Cunningham, R. T. Tetrahedron Lett. 1990, 31, 7587
48. Yamamoto, K.; Suzuki, S.; Tsuji, J. Tetrahedron Lett. 1980, 21, 1653
49. Ricci, A.; Degl'Innocenti, A.; Chimichi, S.; Fiorenza, M.; Rossini, G.; Bestmann, H. J. J. Org. Chem. 1985, 50, 130
50. Obora, Y.; Ogawa, Y.; Imai, Y.; Kawamura, T.; Tsuji, Y. J. Am. Chem. Soc. 2001, 123, 10489
51. Tsubouchi, A.; Onishi, K.; Takeda, T. J. Am. Chem. Soc. 2006, 128, 14268