Palladium(0)-catalyzed amination of allylic natural terpenic functionalized olefins

• Autorzy: Soufiane Houssame , Hafid Anane , Larbi Firdoussi , Abdellah Karim
• Języki publikacji: EN

Abstrakty

EN

The palladium(0) catalyzed amination of allylic acetates and carbonates derivatives from terpenic olefins was carried out under mild conditions. The reaction offers a very good method for the preparation of allylic amines and thus to provide a useful entry to new functionalized terpenic olefin products. The mechanism involving a formation of p-allyl-palladium intermediate complex is in good agreement with the results obtained with the optically active substrates, as well as via an analysis of the observed regio-and stereoselectivity. [...]

Słowa kluczowe

EN

Palladium; Allylic amination; Allylic functionalized terpenic olefin

• Czasopismo: Open Chemistry
• Rocznik: 2008
• Tom: 6
• Numer: 3
• Strony: 470-476

Daty

wydano

2008-09-01

online

2008-08-11

Twórcy

autor

Soufiane Houssame

• Laboratoire de Chimie de Coordination, Faculté des Sciences-Semlalia, Université Cadi Ayyad, BP 2390, Marrakech, Morocco,

autor

Hafid Anane

• Département Sciences de la matière, Faculté Polydisciplinaire de Safi, Route Sidi bouzid, B.P 4162, Safi Université Cadi Ayyad, Morocco

autor

Larbi Firdoussi

• Laboratoire de Chimie de Coordination, Faculté des Sciences-Semlalia, Université Cadi Ayyad, BP 2390, Marrakech, Morocco

autor

Abdellah Karim

• Laboratoire de Chimie de Coordination, Faculté des Sciences-Semlalia, Université Cadi Ayyad, BP 2390, Marrakech, Morocco

Bibliografia

• [1] M. Johannsen, K. A. Jorgensen, Chem. Rev. 98, 1689 (1998) http://dx.doi.org/10.1021/cr970343o[Crossref]
• [2] R. R. Rando, F. Bangerter, J. Am. Chem. Soc. 98, 6762 (1976) http://dx.doi.org/10.1021/ja00437a090[Crossref]
• [3] C.Y.P. Teng, B. Ganem, Tetrahedron Lett. 23, 313 (1982) http://dx.doi.org/10.1016/S0040-4039(00)86818-5[Crossref]
• [4] T. Kondo, H. Nakai, T. Goto, Tetrahedron. 29, 1801 (1973) http://dx.doi.org/10.1016/S0040-4020(01)83202-6[Crossref]
• [5] B. M. Trost, J-P. Genêt, J. Am. Chem. Soc. 98, 8516 (1976) http://dx.doi.org/10.1021/ja00442a034[Crossref]
• [6] B. M. Trost, S. A. Godleski, J-P. Genêt, J. Am. Chem. Soc. 100, 3930 (1978) http://dx.doi.org/10.1021/ja00480a047[Crossref]
• [7] B. M. Trost, D. L. Van vranken, C. Bingel, J. Am. Chem. Soc. 114, 9327 (1992) http://dx.doi.org/10.1021/ja00050a013[Crossref]
• [8] T. Hayashi et al., J. Am. Chem Soc. 111, 6301 (1989) http://dx.doi.org/10.1021/ja00198a048[Crossref]
• [9] B. M. Trost, D. L. Van vranken, C. Bingel, J. Am. Chem. Soc. 115, 444 (1993) http://dx.doi.org/10.1021/ja00055a013[Crossref]
• [10] B. M. Trost, Angew. Chem. 101, 1199 (1989) http://dx.doi.org/10.1002/ange.19891010906[Crossref]
• [11] T. Hayashi, In: I. Ojima (Ed.), Catalytic Asymmetric Synthesis (VCH, New York, 1993) 325
• [12] R. F. Heck, In: A. R. Katritzky, O. Meth-Cohen, C. W. Rees (Eds.), Palladium Reagents in Organic Syntheses (Academic Press, London, 1985) 2
• [13] A. Pfaltz, M. Lautens, In: E. N. Jacobsen, A. Pfaltz, H. Yamamoto (Eds.), Comprehensive Asymmetric Catalysis II (Springer, Berlin, 1999) 833
• [14] J. L. Malleron, J-C. Fiaud, J. Y. Legros, Handbook of Palladium Catalyzed Organic Reaction, (Academic Press, London, 1997)
• [15] Y. J. Shue, S. C. Yang, H. C. Lai, Tetrahedron Lett. 44, 1481 (2003) http://dx.doi.org/10.1016/S0040-4039(02)02861-7[Crossref]
• [16] S. L. You, X. Z. Zhu, Y. M. Luo, X. L. Hou, L. X. Dai, J. Am. Chem. Soc. 123, 7471 (2001) http://dx.doi.org/10.1021/ja016121w[Crossref]
• [17] A. Fihri et al., Adv. Synth. Catal. 347, 1198 (2005) http://dx.doi.org/10.1002/adsc.200505050[Crossref]
• [18] D. H. Nguyen et al., Appl. Organometal. Chem. 20, 845 (2006) http://dx.doi.org/10.1002/aoc.1130[Crossref]
• [19] L. Dubovyk, I. D. G. Watson, A. K. Yudin, J. Am. Chem. Soc. 129, 14172 (2007) http://dx.doi.org/10.1021/ja076659n[Crossref]
• [20] A. M. Johns; Z. Liu; J. F. Hartwig, Angew. Chem. Int. Ed. 46, 7259 (2007) http://dx.doi.org/10.1002/anie.200701899[Crossref]
• [21] W. H. Zheng, N. Sun, X. L. Hou, Org. Lett. 7, 5151 (2005) http://dx.doi.org/10.1021/ol051882f[Crossref]
• [22] B. M. Trost, M. L. Crawley, Chem. Rev. 103, 2921 (2003) http://dx.doi.org/10.1021/cr020027w[Crossref]
• [23] Z. Lu, S. Ma. Angew. Chem. Int. Ed. 47, 258 (2008) http://dx.doi.org/10.1002/anie.200605113[Crossref]
• [24] J. Muzart, Eur. J. Org. Chem. 3077 (2007) [Crossref]
• [25] G. Muchow, J. M. Brunel, M. Maffei, D. Pardigon, G. Buono, Tetrahedron. 54, 10435. (1998) http://dx.doi.org/10.1016/S0040-4020(98)00496-7[Crossref]
• [26] N. Uesaka, F. Saitoh, M. Mori, M. Shibasaki, K. Okamura, T. Date, J. Org. Chem. 59, 5633 (1994) http://dx.doi.org/10.1021/jo00098a022[Crossref]
• [27] Watanabe et al, J. Essent. Oil. Res. 9, 441 (1994) [Crossref]
• [28] S. Elhoussame et al., J. Mol. Catal. A. 168, 15 (2001) http://dx.doi.org/10.1016/S1381-1169(00)00381-2[Crossref]
• [29] H. Ziyat et al., Acta Chim. Slov. 51, 223 (2004)
• [30] L. Elfirdoussi et al., J. Mol. Catal. A. 135, 11 (1998) http://dx.doi.org/10.1016/S1381-1169(97)00285-9[Crossref]
• [31] N. Fdil et al., J. Mol. Catal. A. 108, 15 (1996) http://dx.doi.org/10.1016/1381-1169(95)00284-7[Crossref]
• [32] J. A. Gonçalves, O. V. Howarth, E. V. Gusevskaya, J. Mol. Catal. A. 185, 97 (2002) http://dx.doi.org/10.1016/S1381-1169(02)00061-4[Crossref]
• [33] M. J. Da Silva, J. A. Gonçalves, R. B. Alves, O. V. Howarth, E. V. Gusevskaya, J. Organomet. Chem. 689, 302 (2004) http://dx.doi.org/10.1016/j.jorganchem.2003.10.016[Crossref]
• [34] J. A. Gonçalves, E. V. Gusevskaya, Appl. Catal. A. 258, 93 (2004) http://dx.doi.org/10.1016/j.apcata.2003.08.015[Crossref]
• [35] A. J. Chalk, In: P. N. Rylander, H. Greenfield, R. L. Augustine (Eds.), Catalysis of Organic Reactions (Marcel Dekker, New York, 1988)
• [36] C. Chapuis, D. Jacoby, Appl. Catal. A. 212, 93 (2001)
• [37] H. Mimoun, Chimia. 50, 620 (1996)
• [38] R. D. Connell, T. Rein, B. Akermark, P. Helquist, J. Org. Chem. 53, 3845 (1998) http://dx.doi.org/10.1021/jo00251a035[Crossref]
• [39] B. M. Trost, E. Keinan, J. Am. Chem. Soc. 100, 7779 (1978) http://dx.doi.org/10.1021/ja00492a084[Crossref]
• [40] B. M. Trost, E. Keinan, J. Org. Chem. 44, 3451 (1979) http://dx.doi.org/10.1021/jo01334a001[Crossref]
• [41] J. Tsuji, K. Sato, H. Okumoto, J. Org. Chem. 8, 1341 (1984) http://dx.doi.org/10.1021/jo00182a005[Crossref]
• [42] B. M. Trost, D. L. Van vranken, Chem. Rev. 96, 395 (1996) http://dx.doi.org/10.1021/cr9409804[Crossref]
• [43] O. Piechaczyk, C. Thoumazet, Y. Jean, P. Le Floch, J. Am. Chem. Soc. 128, 14306 (2006) http://dx.doi.org/10.1021/ja0621997[Crossref]

Identyfikatory

DOI

10.2478/s11532-008-0042-3