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Journal
2010 | 8 | 6 | 1210-1215
Article title

Sulfoxides in the allylation of aldehydes in the presence of silicon tetrachloride and allyltributylstannane

Content
Title variants
Languages of publication
EN
Abstracts
EN
SiCl4 can be conveniently activated by catalytic amounts of dimethyl sulfoxide or other readily-available sulfoxides for the allylation of aromatic, hetero-aromatic and unsaturated aldehydes in the presence of allyltributyl stannane. Chiral aryl methyl sulfoxides have been used to develop asymmetric allylation methods, as well as probe the aldehyde substrate scope.
Publisher

Journal
Year
Volume
8
Issue
6
Pages
1210-1215
Physical description
Dates
published
1 - 12 - 2010
online
8 - 10 - 2010
Contributors
author
  • Department of Chemistry, University of Salerno, 84084, Fisciano (Salerno), Italy, amassa@unisa.it
  • Department of Chemistry, University of Salerno, 84084, Fisciano (Salerno), Italy
  • Department of Chemistry, University of Salerno, 84084, Fisciano (Salerno), Italy
References
  • [1] Y. Yamamoto, N. Asao, Chem. Rev. 93, 2207 (1993) http://dx.doi.org/10.1021/cr00022a010[Crossref]
  • [2] J.A. Marshall, Chem. Rev. 96, 31 (1996) http://dx.doi.org/10.1021/cr950037f[Crossref]
  • [3] S.E. Denmark, J. Fu, Chem. Rev. 103, 2763 (2003) http://dx.doi.org/10.1021/cr020050h[Crossref]
  • [4] W.R. Roush, In: B.M. Trost, I. Fleming, C.H. Heathcock (Eds.), Comprehensive Organic Synthesis (Pergamon, Oxford, UK, 1991) Vol. 2, p. 1 http://dx.doi.org/10.1016/B978-0-08-052349-1.00023-8
  • [5] Y. Yamamoto, N. Asao, Chem. Rev. 93, 2207 (1993) http://dx.doi.org/10.1021/cr00022a010[Crossref]
  • [6] J.A. Marshall, Chem. Rev. 96, 31 (1996) http://dx.doi.org/10.1021/cr950037f[Crossref]
  • [7] H. Sakurai, Synlett 1 (1989)
  • [8] S.E. Denmark, G.L. Beutner Angew. Chem. Int. Ed. 47, 1560 (2008) http://dx.doi.org/10.1002/anie.200604943[Crossref]
  • [9] P.I. Dalko, L. Moisan Angew. Chem. Int. Ed. 43, 5138 (2004) http://dx.doi.org/10.1002/anie.200400650[Crossref]
  • [10] S. Kobayashi, K. Nishio, J. Org. Chem. 59, 6620 (1994) http://dx.doi.org/10.1021/jo00101a021[Crossref]
  • [11] S.E. Denmark, D.M. Coe, N.E. Pratt, B.D. Griedel, J. Org. Chem. 59, 6161 (1994) http://dx.doi.org/10.1021/jo00100a013[Crossref]
  • [12] S.E. Denmark, J.R. Heemstra, Jr., J. Org. Chem. 72, 5668 (2007) http://dx.doi.org/10.1021/jo070638u[Crossref]
  • [13] S.E. Denmark, G.L. Beutner, T. Wynn, M.D. Eastgate, J. Am. Chem. Soc. 127, 3774 (2005) http://dx.doi.org/10.1021/ja047339w[Crossref]
  • [14] S.E. Denmark, Y. Fan, J. Org. Chem. 70, 9667 (2005) http://dx.doi.org/10.1021/jo050549m[Crossref]
  • [15] S.E. Denmark, G.L. Beutner J. Am. Chem. Soc. 125, 7800 (2003) http://dx.doi.org/10.1021/ja035448p[Crossref]
  • [16] S.E. Denmark, T. Wynn, G.L. Beutner J. Am. Chem. Soc. 124, 13405 (2002) http://dx.doi.org/10.1021/ja0282947[Crossref]
  • [17] C. Curti, A. Sartori, L. Battistini, G. Rassu, F. Zanardi, G. Casiraghi, Tetrahedron Letters 50, 3428 (2009) http://dx.doi.org/10.1016/j.tetlet.2009.02.181[Crossref]
  • [18] A. Scettri, M.R. Acocella, L. Palombi, C. Scalera, R. Villano, A. Massa, Adv. Synth. Catal. 348, 2229 (2006) http://dx.doi.org/10.1002/adsc.200606159[Crossref]
  • [19] 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]
  • [20] A. Massa, V. de Sio, R. Villano, M.R. Acocella, L. Palombi, G. Sellitto, A. Peduto, R. Filosa, P. De Caprariis, A. Scettri, Synthesis 4, 643 (2009) http://dx.doi.org/10.1055/s-0028-1087677[Crossref]
  • [21] 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]
  • [22] S.E. Denmark, P.A. Barsanti, K.-T. Wong, R.A. Stavenger, J. Org. Chem. 63, 2428 (1998) http://dx.doi.org/10.1021/jo9801420[Crossref]
  • [23] S.E. Denmark, T. Wynn, B.G. Jellerichs, Angew. Chem. Int. Ed. 40, 2255 (2001) http://dx.doi.org/10.1002/1521-3773(20010618)40:12<2255::AID-ANIE2255>3.0.CO;2-3[Crossref]
  • [24] S.E. Denmark, P.A. Barsanti, G.L. Beutner, T.W. Wilson, Adv. Synth. Catal. 349, 567 (2007) http://dx.doi.org/10.1002/adsc.200600551[Crossref]
  • [25] M. Nakajima, M. Saito, M. Uemura. S. Hashimoto, Tetrahedron Letters 43, 8827 (2002) http://dx.doi.org/10.1016/S0040-4039(02)02229-3[Crossref]
  • [26] A.V. Malkov, M.R. Gordon, S. Stoncius, J. Hussain, P. Kocovsky, Org. Lett. 11, 5390 (2009) http://dx.doi.org/10.1021/ol902148s[Crossref]
  • [27] X. Pu, X. Qi, J.M. Ready, J. Am. Chem. Soc. 131, 10364 (2009) http://dx.doi.org/10.1021/ja9041127[Crossref]
  • [28] S.E. Denmark, Y. Fan, J. Org. Chem. 70, 9667 (2005) http://dx.doi.org/10.1021/jo050549m[Crossref]
  • [29] S.E. Denmark, Y. Fan, J. Am. Chem. Soc. 125, 7825 (2003) http://dx.doi.org/10.1021/ja035410c[Crossref]
  • [30] S.E. Denmark, T. Wynn, J. Am. Chem. Soc. 123, 6199 (2001) http://dx.doi.org/10.1021/ja016017e[Crossref]
  • [31] K. Nakanishi, S. Kotani, M. Sugiura, M. Nakajima, Tetrahedron 64, 6415 (2008) http://dx.doi.org/10.1016/j.tet.2008.04.078[Crossref]
  • [32] C.M. Carreno, G. Hernandez-Torres, M. Ribagorda, A. Urbano, Chem. Commun. 41, 6129 (2009) http://dx.doi.org/10.1039/b908043k[Crossref]
  • [33] A. Massa, A.V. Malkov, P. Kocovsky, A. Scettri, Tetrahedron Lett. 44, 7179 (2003) http://dx.doi.org/10.1016/S0040-4039(03)01801-X[Crossref]
  • [34] G. J. Rowlands, W.K. Barnes, Chem. Commun. 2712 (2003) [Crossref]
  • [35] A. Massa, M.R. Acocella, V.D. Sio, R. Villano, A. Scettri, Tetrahedron: Asymmetry 20, 202 (2009) http://dx.doi.org/10.1016/j.tetasy.2009.01.023[Crossref]
  • [36] P. Wang, J. Chen, L. Cun, J. Deng, J. Zhu, J. Liao, Org. Biomol. Chem. 7, 3741 (2009) http://dx.doi.org/10.1039/b909850j[Crossref]
  • [37] V. De Sio, A. Massa, A. Scettri, Org. Biomol. Chem. 8, 3055 (2010) http://dx.doi.org/10.1039/c002988b[Crossref]
  • [38] A. Massa, V. Mazza, A. Scettri, Tetrahedron: Asymmetry 16, 2271 (2005) http://dx.doi.org/10.1016/j.tetasy.2005.05.015[Crossref]
  • [39] S. Kobayashi, C. Ogana, H. Konishi, M. Sugiura, J. Am. Chem. Soc. 125, 6610 (2003) http://dx.doi.org/10.1021/ja035061m[Crossref]
  • [40] I. Fernandez, V. Valdivia, B. Gori, F. Alcudia, E. Alvarez, N. Khiar, Org. Lett. 7, 1307 (2005) http://dx.doi.org/10.1021/ol050080h[Crossref]
  • [41] G. Modena, U. Quintily, G. Scorrano, J. Am. Chem. Soc. 94, 202 (1972) http://dx.doi.org/10.1021/ja00756a036[Crossref]
  • [42] S.E. Denmark, B.M. Eklov, P.J. Yao, M.D. Eastgate, J. Am. Chem. Soc. 131, 11770 (2009) http://dx.doi.org/10.1021/ja902474j[Crossref]
Document Type
Publication order reference
Identifiers
YADDA identifier
bwmeta1.element.-psjd-doi-10_2478_s11532-010-0099-7
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