Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2010 Mar 19;12(6):1184-7.
doi: 10.1021/ol902923e.

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

Paramita Mukherjee  1 , Ross A Widenhoefer
Affiliations

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.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1
Scheme 2
Scheme 2
Scheme 3
Scheme 3
Scheme 4
Scheme 4
Scheme 5
Scheme 5
See this image and copyright information in PMC

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

Publication types