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. 2010 Mar 19;12(6):1184-7.
doi: 10.1021/ol902923e.

Gold(I)-catalyzed amination of allylic alcohols with cyclic ureas and related nucleophiles

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Gold(I)-catalyzed amination of allylic alcohols with cyclic ureas and related nucleophiles

Paramita Mukherjee et al. Org Lett. .

Abstract

A 1:1 mixture of [P(t-Bu)(2)-o-biphenyl]AuCl and AgSbF(6) catalyzes the intermolecular amination of allylic alcohols with 1-methylimidazolidin-2-one and related nucleophiles that, in the case of gamma-unsubstituted or gamma-methyl-substituted allylic alcohols, occurs with high gamma-regioselectivity and syn-stereoselectivity.

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References

    1. Johannsen M, Jørgensen KA. Chem Rev. 1998;98:1689. - PubMed
    1. Lu X, Lu L, Sun J. J Mol Catal. 1987;41:245.
    2. Lu X, Jiang X, Tao X. J Organomet Chem. 1988;344:109.
    3. Masuyama Y, Takahara JP, Kurusu Y. J Am Chem Soc. 1988;110:4473.
    4. Masuyama Y, Kagawa M, Kurusu Y. Chem Lett. 1995:1121.
    5. Itoh K, Hamaguchi N, Miura M, Nomura M. J Chem Soc, Perkin Trans. 1992;1:2833.
    6. Satoh T, Ikeda M, Miura M, Nomura M. J Org Chem. 1997;62:4877. - PubMed
    7. Yang SC, Hung CW. J Org Chem. 1999;64:5000. - PubMed
    8. Yang SC, Tsai YC, Shue YJ. Organometallics. 2001;20:5326.
    9. Shue YJ, Yang SC, Lai HC. Tetrahedron Lett. 2003;44:1481.
    10. Stary I, Star IG, Kocovsky P. Tetrahedron Lett. 1993;34:179.
    11. Tsay S, Lin LC, Furth PA, Shum CC, King DB, Yu SF, Chen B, Hwu JR. Synthesis. 1993:329.
    12. Kimura M, Tomizawa T, Horino Y, Tanaka S, Tamaru Y. Tetrahedron Lett. 2000;41:3627.
    13. Kimura M, Horino Y, Mukai R, Tanaka S, Tamaru Y. J Am Chem Soc. 2001;123:10401. - PubMed
    14. Kimura M, Futamata M, Shibata K, Tamaru Y. Chem Commun. 2003:234. - PubMed
    1. Ozawa F, Okamoto H, Kawagishi S, Yamamoto S, Minami T, Yoshifuji M. J Am Chem Soc. 2002;124:10968. - PubMed
    1. Muzart J. Eur J Org Chem. 2007:3077.
    2. Kinoshita H, Shinokubo H, Oshima K. Org Lett. 2004;6:4085. - PubMed
    3. Ozawa F, Ishiyama T, Yamamoto S, Kawagishi S, Murakami H, Yoshifuji M. Organometallics. 2004;23:1698.
    4. Kayaki Y, Koda T, Ikariya T. J Org Chem. 2004;69:2595. - PubMed
    5. Piechaczyk O, Doux M, Ricard L, le Floch P. Organometallics. 2005;24:1204.
    6. Thoumazet C, Grützmacher H, Deschamps B, Ricard L, le Floch P. Eur J Inorg Chem. 2006:3911.
    7. Piechaczyk O, Thoumazet C, Jean Y, le Floch P. J Am Chem Soc. 2006;128:14306. - PubMed
    8. Mora G, Deschamps B, van Zutphen S, Le Goff XF, Ricard L, le Floch P. Organometallics. 2007;26:1846.
    9. Usui I, Schmidt S, Keller M, Breit B. Org Lett. 2008;10:1207. - PubMed
    1. Ohshima T, Miyamoto Y, Ipposhi J, Nakahara Y, Utsunomiya M, Mashima K. J Am Chem Soc. 2009;131:14317. - PubMed
    2. Utsunomiya M, Miyamoto Y, Ipposhi J, Ohshima T, Mashima K. Org Lett. 2007;9:3371. - PubMed
    3. Mora G, Piechaczyk O, Houdard R, Mezailles N, Le Goff XF, le Floch P. Chem Eur J. 2008;14:10047. - PubMed

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