Trialkylsilyl triflimides as easily tunable organocatalysts for allylation and benzylation of silyl carbon nucleophiles with non-genotoxic reagents

Tetrahedron Letters

Volumn 51, Issue 19, 2010, Pages 2571-2575

  Mendoza, Oscar ^a   Rossey, Guy ^b   Ghosez, Léon ^a  

^a UNIVERSITÉ DE BORDEAUX   (France)

^b SANOFI   (France)

Author keywords

Allylation; Benzylation; Green chemistry; Triflimide

Indexed keywords

ALLYL ACETATE; BENZYL ACETATE; CARBON; ELECTROPHILE; FURAN; IMIDE; INDOLE; NUCLEOPHILE; PYRROLE; REAGENT; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; BENZYLATION; CATALYSIS; CATALYST; COMPLEX FORMATION; ELECTRON TRANSPORT; STEREOSPECIFICITY;

EID: 77950371598     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.03.030     Document Type: Article

References (61)

1. Reviews:. Reetz M.T. Angew. Chem., Int. Ed. Engl. 21 (1982) 96-108
2. Kobayashi S., Wanabe K., Ishitani H., and Matsuo J.-I. In: Fleming I. (Ed). Science of Synthesis, Houben-Weyl Methods of Molecular Transformations Vol. 4 (2002), Thieme, Stuttgart 317-369
3. Fleming I. Pure Appl. Chem. 55 (1983) 1707-1713
4. Hosomi A. Acc. Chem. Res. 21 (1988) 200-206
5. Sarkar T.K. In: Fleming I. (Ed). Science of Synthesis, Houben-Weyl Methods of Molecular Transformations Vol. 4 (2002), Thieme, Stuttgart
6. See also:. Mayr H., and Pock R. Tetrahedron 42 (1986) 4211-4214
7. Dau-Schmidt J.P., and Mayr H. Chem. Ber. 127 (1994) 205
8. Mayr H., Gorath G., and Bauer B. Angew. Chem., Int. Ed. Engl. 33 (1994) 788-789
9. AgOTf:. Takeda K., Ayabe A., Kawashima H., and Harigaya Y. Tetrahedron Lett. 33 (1992) 951-952
10. Black, T.; Stubbs, K. A.; Stick, R. V.; Weibel, J. M.; Pale, P. e-EROS Encyclopedia of Reagents for Organic Synthesis, 2007.
11. 3:. Cella J.A. J. Org. Chem. 47 (1982) 2125-2130
12. 3:. Rubin M., and Gevorgyan V. Org. Lett. 3 (2001) 2705-2707
13. Schwier T., Rubin M., and Gevorgyan V. Org. Lett. 6 (2004) 1999-2001
14. De S.K., and Gibbs R.A. Tetrahedron Lett. 46 (2005) 8345-8350
15. 2:. Kaur G., Kaushik M., and Trehan S. Tetrahedron Lett. 38 (1997) 2521-2524
16. 3:. Kim S.H., Shin C., Pai A.N., Koh H.K., Chang M.H., Chung B.Y., and Cho Y.S. Synthesis (2004) 1581-1584
17. 3. Yasuda M., Saito T., Ueba M., and Baba A. Angew. Chem., Int. Ed. 43 (2004) 1414-1416
18. Saito T., Nishimoto Y., Yasuda M., and Baba A. J. Org. Chem 71 (2006) 8516-8522
19. Saito T., Nishimoto Y., Yasuda M., and Baba A. J. Org. Chem. 72 (2007) 8588-8590
20. 4:. Ying B., Trogden B.G., Kohlman D.T., Liang S.X., and Xu Y. Org. Lett. 6 (2004) 1523-1526
21. 2:. Miyachi H., Nomura M., Tanase T., Takahashi Y., Ide T., Tsunoda M., Murakami K., and Awano K. Bioorg. Med. Chem. Lett. 12 (2002) 77-80
22. Nomura M., Tanase T., Ide T., Tsunoda M., Suzuki M., Uchiki H., Murakami K., and Miyachi H. J. Med. Chem. 46 (2003) 3581-3599
23. Usui S., Fujieda H., Suzuki T., Yoshida N., Nakagawa H., and Miyata N. Bioorg. Med. Chem. Lett. 16 (2006) 3249-3254
24. Usui S., Fujieda H., Suzuki T., Yoshida N., Nakagawa H., Ogura M., Makishima M., and Miyata N. Chem. Pharm. Bull. 55 (2007) 1053-1059
25. Organotin perfluorooctanesulfonates:. An L., Peng Z., Orita A., Kurita A., Man-e S., Ohkubo K., Li X., Fukuzumi S., and Otera J. Chem. Eur. J. 12 (2006) 1642-1647
26. rhodium complex:. Soga T., Takenoshita H., Yamada M., and Mukaiyama T. Bull. Chem. Soc. Jpn. 63 (1990) 3122-3131
27. 2:. Hayashi M., Inubushi A., and Mukaiyama T. Chem. Lett. (1987) 1975-1978
28. 4:. Sharma G.V.M., Reddy K.L., Lakshmi P.S., Ravi R., and Kunwar A.C. J. Org. Chem. 71 (2006) 3967-3969
29. 2:. Reetz M.T., Walz P., Huebner F., Huettenhain S.H., and Heimbach H. Chem. Ber. 117 (1984) 322-335
30. Collins D.J., and Jacobs H.A. Aust. J. Chem. 39 (1986) 2095-2110
31. Grieco P.A., and Handy S.T. Tetrahedron Lett. 38 (1997) 2645-2648
32. Iovel I., Mertins K., Kischel J., Zapf A., and Beller M. Angew. Chem., Int. Ed. 44 (2005) 238-242 Angew. Chem., Int. Ed. 2005, 44, 3913-3917
33. De Surya K., and Richard A.G. Tetrahedron Lett. 46 (2005) 8345-8350
34. Motokura K., Nakagiri N., Mizugaki T., Ebitani K., and Kaneda K. J. Org. Chem. 72 (2007) 6006-6015
35. Rubenbauer P., Herdtweck E., Strassner T., and Bach T. Angew. Chem., Int. Ed. 47 (2008) 10106-10109
36. Mathieu B., and Ghosez L. Tetrahedron Lett. 38 (1997) 5497-5500
37. Mathieu B., de Fays L., and Ghosez L. Tetrahedron Lett. 41 (2000) 9561-9564
38. See also:. Simchen G., and Jonas S. J. Prakt. Chem. 340 (1998) 506-512
39. Ishii A., Kotera O., Saeki T., and Mikami K. Synlett (1997) 1145-1146
40. Mikami K., Kotera O., Motoyama Y., and Tanaka M. Inorg. Chem. Commun. 1 (1998) 10-11
41. Ishihara K., Hiraiwa Y., and Yamamoto H. Synlett (2001) 1851-1854
42. Ishihara K., Hiraiwa Y., and Yamamoto H. Chem. Commun. (2002) 1564-1565
43. Ishihara K., and Hiraiwa Y. Eur. J. Org. Chem. (2006) 1837-1844
44. See also:. Hara K., Akiyama R., and Sawamura M. Org. Lett. 7 (2005) 5621-5623
45. Kuhnert N., Peverley J., and Robertson J. Tetrahedron Lett. 39 (1998) 3215-3216
46. Cossy J., Lutz F., Alauze V., and Meyer C. Synlett (2002) 45-48
47. Yu C.-M., Lee J.-Y., So B., and Hong J. Angew. Chem., Int. Ed. 41 (2002) 161-163
48. Mathieu B., and Ghosez L. Tetrahedron 58 (2002) 8219-8226
49. Inanaga K., Takasu K., and Ihara M. J. Am. Chem. Soc. 127 (2005) 3668-3669
50. Othman R.B., Bousquet T., Othman M., and Dalla V. Org. Lett. 7 (2005) 5335-5337
51. Tranchant M.J., Moine C., Othman R.B., Bousquet T., Othman M., and Dalla V. Tetrahedron Lett. 47 (2006) 4447-4480
52. Takasu K., Hosokawa N., Inanaga K., and Ihara M. Tetrahedron Lett. 47 (2006) 6053-6056
53. Jung M.E., and Ho D.G. Org. Lett. 9 (2007) 375-378
54. Dudnick A.S., and Gevorgyan V. Angew. Chem., Int. Ed. 46 (2007) 5195-5197
55. Takasu K., Miyakawa Y., Ihara M., and Tokuyama H. Chem. Pharm. Bull. 56 (2008) 1205-1206
56. Turks M., and Vogel P. J. Org. Chem. 74 (2009) 435-437
57. Commandeur M., Commandeur C., De Paolis M., Edmunds A.J.F., Maienfisch P., and Ghosez L. Tetrahedron Lett. 50 (2009) 3359-3362
58. Tang Z., Mathieu B., Tinant B., Dive G., and Ghosez L. Tetrahedron 63 (2007) 8449-8462 See also Ref. 2b
59. Garcia-Garcia P., Lay F., Garcia-Garcia P., Rabalakos C., and List B. Angew. Chem., Int. Ed. 48 (2009) 4363-4366
60. 2 in dichloromethane. For large-scale experiments, triflimide was introduced as a solid. Therefore, one can say that in most cases, the reaction can be performed in the absence of solvent.
61. 2 were added into a 5-mL round-bottomed flask equipped with a magnetic stirbar, 410 μL of anisyl acetate (2.5 mmol) and 583 μL of trimethyl cyclohexenyloxysilane (3.0 mmol). After 5 min the solvent was evaporated and the crude mixture was purified by column chromatography (silicagel, eluent: cyclohexane/ethyl acetate 9:1) to obtain a pure colourless oil in 85% yield.