Radical Allylation with α‐Branched Allyl Sulfones
2008; Wiley; Volume: 47; Issue: 49 Linguagem: Inglês
10.1002/anie.200804298
ISSN1521-3773
AutoresNicolas Charrier, Samir Z. Zard,
Tópico(s)Synthetic Organic Chemistry Methods
ResumoAngewandte Chemie International EditionVolume 47, Issue 49 p. 9443-9446 Communication Radical Allylation with α-Branched Allyl Sulfones† Nicolas Charrier, Nicolas Charrier Laboratoire de Synthèse Organique associé au CNRS, Ecole Polytechnique, 91128 Palaiseau Cedex (France), Fax: (+33) 169335972Search for more papers by this authorSamir Z. Zard Prof., Samir Z. Zard Prof. [email protected] Laboratoire de Synthèse Organique associé au CNRS, Ecole Polytechnique, 91128 Palaiseau Cedex (France), Fax: (+33) 169335972Search for more papers by this author Nicolas Charrier, Nicolas Charrier Laboratoire de Synthèse Organique associé au CNRS, Ecole Polytechnique, 91128 Palaiseau Cedex (France), Fax: (+33) 169335972Search for more papers by this authorSamir Z. Zard Prof., Samir Z. Zard Prof. [email protected] Laboratoire de Synthèse Organique associé au CNRS, Ecole Polytechnique, 91128 Palaiseau Cedex (France), Fax: (+33) 169335972Search for more papers by this author First published: 20 November 2008 https://doi.org/10.1002/anie.200804298Citations: 35 † N.C. thanks the French Ministère de l'Education Nationale, de la Recherche et de la Technologie for a fellowship. Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Graphical Abstract Branching out with sulfones: The use of allyl isopropyl sulfones solves the problem of premature isomerization and allows the radical addition of xanthates to α-branched allyl sulfones (see scheme; DCE=1,2-dichloroethane, TMS=trimethylsilyl). Highly functionalized structures can thus be rapidly assembled under mild reaction conditions by using cheap and readily available substrates and reagents. References 1 1aJ. Grignon, M. Pereyre, J. Organomet. Chem. 1973, 61, C 33–C 35; 1bM. Kosugi, K. Kurino, K. Takayama, T. Migita, J. Organomet. Chem. 1973, 56, C 11–C 13. 2 2aJ. Grignon, M. Pereyre, J. Organomet. Chem. 1973, 61, C 33–C 35; 2bM. Kosugi, K. Kurino, K. Takayama, T. Migita, J. Organomet. Chem. 1973, 56, C 11–C 13; 2cG. E. Keck, J. B. Yates, J. Am. Chem. Soc. 1982, 104, 5829– 5831; 2dG. E. Keck, E. J. Enholm, D. F. Kachensky, Tetrahedron Lett. 1984, 25, 1867– 1870; 2eG. E. Keck, E. J. Enholm, J. B. Yates, M. R. Wiley, Tetrahedron 1985, 41, 4079– 4094; 2fG. E. Keck, D. F. Kachensky, E. J. Enholm, J. Org. Chem. 1985, 50, 4317– 4325. 3J. E. Baldwin, R. M. Adlington, D. J. Birch, J. A. Crawford, J. B. Sweeney, J. Chem. Soc. Chem. Commun. 1986, 1339– 1340. 4For exceptions, see: 4aG. A. Russell, L. L. Herold, J. Org. Chem. 1985, 50, 1037– 1040; 4bT. Migita, K. Nagai, M. Kosugi, Bull. Chem. Soc. Jpn. 1983, 56, 2480– 2484; 4cH. Fliri, C.-P. Mak, J. Org. Chem. 1985, 50, 3438– 3442; 4dC. J. Easton, I. M. Scharfbillig, J. Org. Chem. 1990, 55, 384– 386; 4eY. Watanabe, T. Yoneda, T. Okumura, Y. Ueno, T. Toru, Bull. Chem. Soc. Jpn. 1993, 66, 3030– 3033; 4fY. Yoshida, N. Ono, F. Sato, J. Org. Chem. 1994, 59, 6153– 6155; 4gI. Ryu, S. Kreimerman, T. Niguma, S. Minakata, M. Komatsu, Z. Luo, D. P. Curran, Tetrahedron Lett. 2001, 42, 947– 950. 5M. D. Johnson, Acc. Chem. Res. 1983, 16, 343– 349. 6S. I. Usugi, H. Yorimitsu, K. Oshima, Tetrahedron Lett. 2001, 42, 4535– 4538. 7C. C. Huval, D. A. Singleton, Tetrahedron Lett. 1993, 34, 3041– 3042. 8 8aG. E. Keck, J. H. Byers, J. Org. Chem. 1985, 50, 5442– 5444; 8bA. Yanagisawa, Y. Noritake, H. Yamamoto, Chem. Lett. 1988, 1899– 1902; 8cP. Breuilles, D. Uguen, Tetrahedron Lett. 1990, 31, 357– 360. 9For emphasis on the problems linked with tin-mediated radical chemistry, see: P. A. Baguley, J. C. Walton, Angew. Chem. 1998, 110, 3272– 3283; Angew. Chem. Int. Ed. 1998, 37, 3072– 3082. 10One notable exception is the elegant use of a branched allyl sulfone in the total synthesis of (+)-pseudomonic acid C: G. E. Keck, A. M. Tafesh, J. Org. Chem. 1989, 54, 5845– 5846. 11It is, for example, possible to combine an atom- or group-transfer radical addition to allylsilanes with a fluoride-induced elimination, see: 11aN. A. Porter, G. Zhang, A. D. Reed, Tetrahedron Lett. 2000, 41, 5773– 5777; 11bL. Chabaud, Y. Landais, P. Renaud, Org. Lett. 2002, 4, 4257– 4270; 11cM. E. Briggs, S. Z. Zard, Synlett 2005, 334– 336. 12 12aF. Bertrand, F. Le Guyader, L. Liguori, G. Ouvry, B. Quiclet-Sire, S. Seguin, S. Z. Zard, C. R. Acad. Sci. II 2001, 4, 547– 555; 12bF. Le Guyader, B. Quiclet-Sire, S. Seguin, S. Z. Zard, J. Am. Chem. Soc. 1997, 119, 7410– 7411; 12cB. Quiclet-Sire, S. Seguin, S. Z. Zard, Angew. Chem. 1998, 110, 3056– 3058; Angew. Chem. Int. Ed. 1998, 37, 2864– 2867. 13For reviews on xanthate chemistry, see: 13aB. Quiclet-Sire, S. Z. Zard, Top. Curr. Chem. 2006, 264, 201– 236; 13bS. Z. Zard in Radicals in Organic Synthesis Vol. 1 (Eds.: ), Wiley-VCH, Weinheim, 2001, pp. 90– 108; 13cB. Quiclet-Sire, S. Z. Zard, Phosphorus Sulfur Silicon 1999, Vol. 153–154, 137– 154; 13dB. Quiclet-Sire, S. Z. Zard, J. Chin. Chem. Soc. 1999, 46, 139– 145; 13eS. Z. Zard, Angew. Chem. 1997, 109, 724– 737; Angew. Chem. Int. Ed. Engl. 1997, 36, 672– 685. 14O. Bergeot, C. Corsi, M. El Qacemi, S. Z. Zard, Org. Biomol. Chem. 2006, 4, 278– 290. 15B. Quiclet-Sire, G. Ouvry, S. Z. Zard, Angew. Chem. 2006, 118, 5124– 5128; Angew. Chem. Int. Ed. 2006, 45, 5002– 5006. 16See for example: B. M. Trost, C. A. Merlic, J. Org. Chem. 1990, 55, 1127– 1129. Citing Literature Volume47, Issue49November 24, 2008Pages 9443-9446 ReferencesRelatedInformation
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