Iodoaminations of alkenes

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Wirth, Thomas ; Mizar, Pushpak (2017)

The activation of alkenes and their subsequent functionalization is a frequently used methodology in synthetic chemistry. This review highlights recent iodine-mediated aminations and elaborates on the various strategies to bring about regio- or stereoselective transformations.
  • References (25)
    25 references, page 1 of 3

    Bougault, M. J. R. Acad. Sci. 1904, 139, 864.

    (a) Qiu, J.; Silverman, R. B. J. Med. Chem. 2000, 43, 706; (b) Pors, K.; Shnyder, S. D.; Teesdale-Spittle, P. H.; Hartley, J. A.; Zloh, M.; Searcey, M.; Patterson, L. H. J.

    Med. Chem. 2006, 49, 7013; (c) Kuang, Y.; Balakrishnan, K.; Gandhi, V.; Peng, X. J. Am. Chem. Soc. 2011, 133, 19278.

    (3) Selected reviews: (a) French, A. N.; Bissmire, S.; Wirth, T. Chem. Soc. Rev. 2004, 33, 354; (b) Chen, G.; Ma, S. Angew. Chem. 2010, 122, 8484; Angew. Chem. Int. Ed. 2010, 49, 8306; (c) Castellanos, Fletcher, A. S. P. Chem. Eur. J. 2011, 17, 5766; (d) Tan, C. K.; Zhou, L.; Yeung, Y.-Y. Synlett 2011, 1335.

    (4) (a) Hennecke, U. Chem. Asian J. 2012, 7, 456; (b) Haas, J.; Piguel, S.; Wirth, T. Org. Lett. 2002, 4, 297; (c) Haas, J.; Bissmire, S.; Wirth, T. Chem. Eur. J. 2005, 11, 5777.

    (5) For reviews of halocyclizations, see: (a) Bartlett, P. A. In Asymmetric Synthesis, Ed. Morrison, J. D. Academic Press, Orlando, 1984, 3, 411; (b) Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321; (c) Harding, K. E.; Tiner, T. H. Comprehensive Organic Synthesis, Eds. Trost, B. M.; Fleming, I. Pergamon Press, New York, 1991, Vol. 4, p 363.

    (6) (a) Schmid, G. H.; Garratt, D. G. The Chemistry of Double- Bonded Functional Groups, Part 2; Ed.: Patai, S. Wiley, New York, 1977, 725; (b) Schmid, G. H. The Chemistry of Double-Bonded Functional Groups, Vol. 2, Part 1, Ed.: Patai, S. Wiley, New York, 1989, 679.

    (7) (a) Harding, K. E.; Marman, T. H.; Nam, D. Tetrahedron 1988, 44, 5605; (b) Zefirov, N. S. Tetrahedron 1977, 33, 2719; (c) Rychnowsky, S. D.; Bartlett, P. A. J. Am. Chem. Soc. 1981, 103, 3963.

    (8) (a) Olah, G. A.; Bollinger, J. M. J. Am. Chem. Soc. 1967, 89, 4744; (b) Olah, G. A.; Bollinger, J. M. J. Am. Chem. Soc. 1968, 90, 947; (c) Olah, G. A.; Bollinger, J. M.; Brinich, J. J. Am. Chem. Soc. 1968, 90, 2587.

    (9) (a) Brown, R. S.; Nagorski, R. W.; Bennet, A. J.; McClung, R. E. D.; Aarts, G. H. M.; Klobukowski, M.; McDonald, R.; Santarsiero, B. D. J. Am. Chem. Soc. 1994, 116, 2448; (b) Neverov, A. A.; Brown, R. S. J. Org. Chem. 1996, 61, 962; (c) Brown, R. S. Acc. Chem. Res. 1997, 30, 131; (d) Denmark, S. E.; Kuester, W. E.; Burk, M. T. Angew. Chem. 2012, 124, 11098; Angew. Chem. Int. Ed. 2012, 51, 10938.

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