Mukaiyama-Michael vinylogous additions to nitroalkenes under solvent-free conditions

• Authors: Arrigo Scettri , Rosaria Villano , Patrizia Manzo , Maria Acocella
• Languages of publication: EN

Abstracts

EN

The first Mukaiyama-Michael vinylogous reaction of a dioxinone-derived silyl ether to nitroalkenes is reported. The conjugate addition is performed in absence of any catalyst under solvent-free conditions, proceeding with satisfactory efficiency with variously substituted nitroalkenes.Moreover, the first organocatalyzed Mukaiyama-Michael vinylogous reaction of trimethylsilyloxyfuran to nitroalkenes is described.The reaction is promoted by Brønsted acids under solvent-free conditions, taking place in moderate to good yield with variously substituted nitroalkenes..

Keywords

EN

Organocatalysis; Trimethylsilyloxyfuran; Dioxinone-derived silyl ether; Brønsted acids; Nitroalkenes

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2012
• Volume: 10
• Issue: 1
• Pages: 47-53

Dates

published

1 - 2 - 2012

online

24 - 11 - 2011

Contributors

author

Arrigo Scettri

• University of Salerno

author

Rosaria Villano

• Reg. Baldinca

author

Patrizia Manzo

• University of Salerno

author

Maria Acocella

• University of Salerno

References

• [1] J. Christoffers, Eur. J. Org. Chem. 1259 (1998)
• [2] N. Krause, A. Hoffmann-Röder, Synthesis 171 (2001)
• [3] J. Christoffers, Synlett 723 (2001)
• [4] H. Yang, S. Kim, Synlett 555 (2008)
• [5] M. Sibi, S. Mangem, Tetrahedron 56, 8033 (2000) http://dx.doi.org/10.1016/S0040-4020(00)00618-9[Crossref]
• [6] O.M. Berner, L. Tedeschi, D. Enders, Eur. J. Org. Chem. 1877 (2002)
• [7] N. Ono, In: H. Feuer (Ed), The Nitro Group in Organic Synthesis (Wiley-VCH, New York, 2001) http://dx.doi.org/10.1002/0471224480[Crossref]
• [8] A.S. Demir, S. Eymur, Tetrahedron: Asymmetry 21, 112 (2010) http://dx.doi.org/10.1016/j.tetasy.2009.12.008[Crossref]
• [9] Y. Zhu, J.P. Malerich, V.H. Rawal, Angew. Chem. Int. Ed. 49, 153 (2010)
• [10] F.A. Luzzio, Tetrahedron 57, 915 (2001) http://dx.doi.org/10.1016/S0040-4020(00)00965-0[Crossref]
• [11] G. Rosini, In: B.M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis (Pergamon press, New York, 1991) Vol. 2, p. 321 http://dx.doi.org/10.1016/B978-0-08-052349-1.00032-9[Crossref]
• [12] H.W. Pimuk, Org. React. 38, 685 (1990)
• [13] J.U. Nef, Justus Liebigs Ann. Chem. 210, 263 (1894) http://dx.doi.org/10.1002/jlac.18942800209[Crossref]
• [14] R. Tamura, A. Kamimura, N. Ono, Synthesis 423 (1991)
• [15] M.A. Poupart, G. Fazal, S. Goulet, L.T. Mar J. Org. Chem. 64, 1356 (1999) http://dx.doi.org/10.1021/jo9815204[Crossref]
• [16] A.G.M. Barrett, C.D. Spilling, Tetrahedron Lett. 29, 5733 (1988) http://dx.doi.org/10.1016/S0040-4039(00)82175-9[Crossref]
• [17] D.H. Layd, D.E. Nichols, J. Org. Chem. 51,4294 (1986) http://dx.doi.org/10.1021/jo00372a037[Crossref]
• [18] B. Raju, R. Ragul, B.N. Sivasankar, Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry 48B, 1315 (2009)
• [19] V. Meyer, C. Wurster, Ber. Dtsch. Chem. Ges. 6, 1168 (1873) http://dx.doi.org/10.1002/cber.18730060294[Crossref]
• [20] M.J. Kamlet, L.A. Kaplan, J.C. Dacons, J. Org. Chem. 26, 4371 (1961) http://dx.doi.org/10.1021/jo01069a046[Crossref]
• [21] T. Mukaiyama, T. Hoshino, J. Am. Chem. Soc. 82, 5339 (1960) http://dx.doi.org/10.1021/ja01505a017[Crossref]
• [22] R. Braslau, G. O’Brian, J. Henise, Y. Thongpaisanwong, E. Murphy, L. Mueller, J. Ruehl, Synthesis, 1496 (2005)
• [23] C. Palomo, S. Vera, A. Mielgo, E. Gómez-Bengoa, Angew. Chem. Int. Ed. 45, 5984 (2006) http://dx.doi.org/10.1002/anie.200602207[Crossref]
• [24] For recent reviews, see
• [25] E.R. Jarno, S.D. Miller, Tetrahedron 58, 2481 (2002) http://dx.doi.org/10.1016/S0040-4020(02)00122-9[Crossref]
• [26] B. List, Tetrahedron 58, 5573 (2002) http://dx.doi.org/10.1016/S0040-4020(02)00516-1[Crossref]
• [27] B. List, Acc. Chem. Res. 37, 548 (2004) http://dx.doi.org/10.1021/ar0300571[Crossref]
• [28] B. List, Chem. Commun. 819 (2006)
• [29] D.M. Barners, J. Ji, M.G. Fickers, M. A. Fitzperald, S.A. King, H.E. Morton, F.A. Plagge, M. Preskill, S.H. Wagaw, S.J. Wittenberg, J. Zhang, J. Am. Chem. Soc. 124, 13097 (2002) http://dx.doi.org/10.1021/ja026788y[Crossref]
• [30] M. Watanobe, A. Ikagawa, H. Wang, K. Murata, T. Ikariya, J. Am. Chem. Soc. 126, 11148 (2004) http://dx.doi.org/10.1021/ja046296g[Crossref]
• [31] D.A. Evans, D. Seidel, J. Am. Chem. Soc. 127, 9958 (2005) http://dx.doi.org/10.1021/ja052935r[Crossref]
• [32] S. Kobayashi, S. Suda, M. Yamada, T. Mukaiyama, Chem. Lett. 23, 97 (1994) http://dx.doi.org/10.1246/cl.1994.97[Crossref]
• [33] A. Bernardi, K. Karamfilova, G. Boschin, C. Scolastico, Tetrahedron Lett. 36, 1363 (1995) http://dx.doi.org/10.1016/0040-4039(94)02478-T[Crossref]
• [34] A. Bernardi, G. Colombo, C. Scolastico, Tetrahedron Lett. 37, 8921 (1996) http://dx.doi.org/10.1016/S0040-4039(96)02048-5[Crossref]
• [35] D.A. Evans, T. Rouis, M.C. Mekazlowski, J.S. Terdrow, J. Am. Chem. Soc. 121, 1994 (1999) http://dx.doi.org/10.1021/ja983864h[Crossref]
• [36] W. Wang, H. Li, J. Wang, Org. Lett. 7, 1637 (2005) http://dx.doi.org/10.1021/ol0503337[Crossref]
• [37] S. E. Denmark, M. Xie, J. Org. Chem. 72, 7050 (2007) http://dx.doi.org/10.1021/jo071126i[Crossref]
• [38] M. De Rosa, M.R. Acocella, R. Villano, A. Soriente, A. Scettri, Tetrahedron: Asymmetry 14, 2499 (2003) http://dx.doi.org/10.1016/S0957-4166(03)00494-4[Crossref]
• [39] M.R. Acocella, A. Massa, L. Palombi, R. Villano, A. Scettri, Tetrahedron Lett. 46, 6141 (2005) http://dx.doi.org/10.1016/j.tetlet.2005.06.152[Crossref]
• [40] M.R. Acocella, M. De Rosa, A. Massa, L. Palombi, R. Villano, A. Scettri, Tetrahedron 61, 4091 (2005) http://dx.doi.org/10.1016/j.tet.2005.02.020[Crossref]
• [41] R. Villano, M.R. Acocella, A. Massa, L. Palombi, A. Scettri, Tetrahedron 63, 12317 (2007) http://dx.doi.org/10.1016/j.tet.2007.09.073[Crossref]
• [42] M. Frings, I. Atodiresci, Y. Wang, J. Runsik, G. Raabe, C. Bolm, Chem. Eur. J. 165, 4577 (2010) http://dx.doi.org/10.1002/chem.200903077[Crossref]
• [43] I. Fleming, T. V. Lee, Tetrahedron Lett. 22, 705 (1981) http://dx.doi.org/10.1016/S0040-4039(01)92530-4[Crossref]
• [44] J. Hassfeld, M. Chistmann, M. Kalesse, Org. Lett. 3, 3561 (2001) http://dx.doi.org/10.1021/ol016677o[Crossref]
• [45] D.M. Speare, S.M. Fleming, M.N. Beckett, J.-J. Li, T.D.H. Bugg, Org. Biomol. Chem. 2, 2942 (2004) http://dx.doi.org/10.1039/b410322j[Crossref]
• [46] S.E. Denmark, J.R. Heemstra, Jr. J. Org. Chem. 72, 5668 (2007) http://dx.doi.org/10.1021/jo070638u[Crossref]
• [47] S.E. Denmark, M. Xie, J. Org. Chem. 72, 7050 (2007) http://dx.doi.org/10.1021/jo071126i[Crossref]
• [48] K. Krohn, J. Diederichs, M. Riaz Tetrahedron 62, 1223 (2006) http://dx.doi.org/10.1016/j.tet.2005.10.063[Crossref]
• [49] H. Uno, A. Masumoto, E. Honda, Y. Nagamachi, Y. Yamaoka, N. Ono, J. Chem. Soc. Perkin Trans 1, 3189 (2001) http://dx.doi.org/10.1039/b104789m[Crossref]
• [50] S. E. Denmark, M. Xie, J. Org. Chem. 72, 7050 (2007) http://dx.doi.org/10.1021/jo071126i[Crossref]
• [51] Y.S. Rao, Chem. Rev. 76, 625 (1976) http://dx.doi.org/10.1021/cr60303a004[Crossref]
• [52] M.V.N. De Souza, Mini-Rev. Org. Chem. 2, 139 (2005) http://dx.doi.org/10.2174/1570193053544427[Crossref]
• [53] N.B. Carter, A.E. Nadany, J.R. Sweeney, J. Chem. Soc. Perkin Trans 1, 2324 (2002) http://dx.doi.org/10.1039/b007664n[Crossref]
• [54] C.W. Jefford, A.W. Sledeski, J. Boukouvalas, Helv. Chim. Acta 72, 1362 (1989) http://dx.doi.org/10.1002/hlca.19890720625[Crossref]
• [55] B. Figadère, C. Chaboche, J. F. Peyrat, A. Cove, Tetrahedon Lett. 34, 8093 (1993) http://dx.doi.org/10.1016/S0040-4039(00)61460-0[Crossref]
• [56] B. Figadère, J.F. Peyrat, A. Cove, J. Org. Chem. 62, 3428 (1997) http://dx.doi.org/10.1021/jo970212n[Crossref]
• [57] S. Hanessian, T.A. Grillo, J. Org. Chem. 63, 1049 (1998) http://dx.doi.org/10.1021/jo9713621[Crossref]
• [58] S. Hanessian, S. Giroux, M. Buffat, Org. Lett. 7, 3989 (2005) http://dx.doi.org/10.1021/ol051483k[Crossref]
• [59] I. Hanna, L. Ricard, Tetrahedron Lett. 40, 863 (1999) http://dx.doi.org/10.1016/S0040-4039(98)02541-6[Crossref]
• [60] C.-W. Cho, M.J. Krische, Angew. Chem. Int. Ed. 6689 (2004)
• [61] N. Maulide, I.E. Marko, Org. Lett. 8, 3705 (2006) http://dx.doi.org/10.1021/ol061284g[Crossref]
• [62] S.-K. Kang, T. Yamaguchi, P.-S. Ho, W.-Y. Kim, S.-K. Yoon, Tetrahedron Lett. 38, 1947 (1997) http://dx.doi.org/10.1016/S0040-4039(97)00230-X
• [63] S.-K. Kang, H.-C. Ryu, Y.-T. Hong, J. Chem. Soc. Perkin Trans 1,20, 3350 (2000). http://dx.doi.org/10.1039/b006431i[Crossref]
• [64] G. Casiraghi, F. Zanardi, G. Appendino, G. Rassu, Chem. Rev. 100, 1929 (2000) http://dx.doi.org/10.1021/cr990247i[Crossref]
• [65] M. Szlosek, B. Figadère, Angew. Chem. Int. Ed. 39, 1799 (2000) http://dx.doi.org/10.1002/(SICI)1521-3773(20000515)39:10<1799::AID-ANIE1799>3.0.CO;2-Z[Crossref]
• [66] S. Onitsuka, Y. Matsuoka, R. Irie, T. Katsuki, Chem. Lett. 32, 974 (2003) http://dx.doi.org/10.1246/cl.2003.974[Crossref]
• [67] L. Palombi, M.R. Acocella, N. Celenta, A. Massa, R. Villano, A. Scettri, Tetrahedron: Asymmetry 17, 3300 (2006) http://dx.doi.org/10.1016/j.tetasy.2006.11.041[Crossref]
• [68] E.L. Carswell, M.L. Snapper, A.H. Hoveyda, Angew. Chem. Int. Ed. 45, 7230 (2006) http://dx.doi.org/10.1002/anie.200603496[Crossref]
• [69] M. De Rosa, L. Citro, A. Soriente, Tetrahedron Lett. 47, 8507 (2006) http://dx.doi.org/10.1016/j.tetlet.2006.09.143[Crossref]
• [70] T. Ollevier, J.E. Bouchard, V. Desyroy J. Org. Chem. 73, 331 (2008) http://dx.doi.org/10.1021/jo702085p[Crossref]
• [71] M.A. Brimble, R.J.R. Elliot, Tetrahedron 53, 7715 (1997) http://dx.doi.org/10.1016/S0040-4020(97)00436-5[Crossref]
• [72] M.C. Carreno, C.G. Luzon, M. Ribagorda, Chem. Eur. J. 8, 208 (2002) http://dx.doi.org/10.1002/1521-3765(20020104)8:1<208::AID-CHEM208>3.0.CO;2-0[Crossref]
• [73] H. Suga, T. Kitamura, A. Kakehi, T. Baba, Chem. Commun. 1414 (2004)
• [74] H. Kitajima, T. Katsuki, Synlett 568 (1997)
• [75] H. Kitajima, T. Katsuki, Tetrahedron 53, 17015 (1997) http://dx.doi.org/10.1016/S0040-4020(97)10152-1[Crossref]
• [76] G. Desimoni, G. Faita S. Filippone, M. Mella, M.G. Zampari, M. Zema, Tetrahedron 57, 10203 (2001) http://dx.doi.org/10.1016/S0040-4020(01)01055-9[Crossref]
• [77] G. Desimoni, G. Faita, M. Guala, A. Laurenti, M. Mella Chem. Eur. J. 11, 3816 (2005) http://dx.doi.org/10.1002/chem.200401213[Crossref]
• [78] T. Fukuyama, S. Goto, Tetrahedron Lett. 30, 6491 (1989) http://dx.doi.org/10.1016/S0040-4039(01)89002-X[Crossref]
• [79] S.P. Brown, N.C. Goodwin, D.W.C. Mac Millan, J. Am. Chem. Soc. 125, 1192 (2003) http://dx.doi.org/10.1021/ja029095q[Crossref]
• [80] B. Simmons, A.M. Walji, C.H. Larsen, D.W.C. MacMillan, Angew. Chem. Int. Ed. 48, 4349 (2009) http://dx.doi.org/10.1002/anie.200900220[Crossref]
• [81] B.M. Trost, J. Hitce, J. Am. Chem. Soc. 131, 4572 (2009) http://dx.doi.org/10.1021/ja809723u[Crossref]
• [82] M. Terada, K. Ando, Org. Lett. 13, 2026 (2011) http://dx.doi.org/10.1021/ol200415u[Crossref]
• [83] N.J.A. Martin, X. Cheng, B. List, J. Am. Chem. Soc. 130, 13862 (2008) http://dx.doi.org/10.1021/ja8069852[Crossref]
• [84] N.J.A. Martin, L. Ozores, B. List, J. Am. Chem. Soc. 129, 8976 (2007) http://dx.doi.org/10.1021/ja074045c[Crossref]
• [85] J. Itoh, K. Fuchibe, T. Akiyama, Angew. Chem. Int. Ed. 47, 4016 (2008) http://dx.doi.org/10.1002/anie.200800770[Crossref]
• [86] P.R. Schreiner, Z. Zhang, Synthesis 2559 (2007)
• [87] S.J. Connon, Angew. Chem. Int. Ed. 45, 3909 (2006) http://dx.doi.org/10.1002/anie.200600529[Crossref]
• [88] T. Akiyama, Chem. Rev. 107, 5744 (2007) http://dx.doi.org/10.1021/cr068374j[Crossref]
• [89] M. Terada Chem. Commun. 4097 (2008)
• [90] A. Scettri, V. De Sio, R. Villano, M.R. Acocella, Synlett 2629 (2009)

Identifiers

DOI

10.2478/s11532-011-0122-7