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
. 2009 Jan 10;65(2):449-455.
doi: 10.1016/j.tet.2008.11.027.

Novel bifunctional sulfonamides catalyze an enantioselective conjugate addition

Patrick G McGarraugh  1 , Stacey E Brenner
Affiliations

Novel bifunctional sulfonamides catalyze an enantioselective conjugate addition

Patrick G McGarraugh et al. Tetrahedron. .

Abstract

A new bifunctional organocatalyst with a novel structural and functional motif has been developed. This bifunctional sulfonamide organocatalyst was used in the conjugate addition of 1,3-dicarbonyl compounds (13) to β-nitrostyrenes (12). Yields up to 91% and enantiomeric excesses up to 79% were obtained in this reaction. This catalyst activates both 13 via its basic moiety and 12 through hydrogen bonding.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Bifunctional organocatalysts with two H-bond donors
Figure 2
Figure 2
Bissulfonamide organocatalysts with two H-bond donors
Figure 3
Figure 3
Novel bissulfonamide organocatalysts
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

References

    1. For recent general reviews, see for example: (a) Enders D, Narine AA. J Org Chem. 2008;73:7857–7870.Dondoni A, Massi A. Angew Chem Int Ed. 2008;47:4638–4660.Melchiorre P, Marigo M, Carlone A, Bartoli G. Angew Chem Int Ed. 2008;47:6138–6171.

    1. For recent reviews, see for example: (a) Doyle AG, Jacobsen EN. Chem Rev. 2007;107:5713–5743.Akiyama T. Chem Rev. 2007;107:5744–5758.

    1. For thioureas derived from 1,2-cyclohexanediamine, see for example: (a) Okino T, Hoashi Y, Takemoto Y. J Am Chem Soc. 2003;125:12672–12673.Berkessel A, Cleemann F, Mukherjee S, Müller TN, Lex J. Angew Chem Int Ed. 2005;44:807–811.Fuerst DE, Jacobsen EN. J Am Chem Soc. 2005;127:8964–8965.Dove AP, Pratt RC, Lohmeijer BGG, Waymouth RM, Hedrick JL. J Am Chem Soc. 2005;127:13798–13799.Li H, Wang J, Zu L, Wang W. Tetrahedron Lett. 2006;47:2585–2589.Liu TY, Li R, Chai Q, Long J, Li BJ, Wu Y, Ding LS, Chen YC. Chem Eur J. 2006;13:319–327.

    1. For thioureas derived from 1,2-diphenylethylenediamine, see for example: (a) Okino T, Hoashi Y, Furukawa T, Xu X, Takemoto Y. J Am Chem Soc. 2005;127:119–125.Liu TY, Long J, Li BJ, Jiang L, Li R, Wu Y, Ding LS, Chen YC. Org Biomol Chem. 2006;4:2097–2099.

    1. For thioureas derived from BINAP, see for example: (a) Wang J, Li H, Yu X, Zu L, Wang W. Org Lett. 2005;7:4293–4296.Wang J, Li H, Duan W, Zu L, Wang W. Org Lett. 2005;7:4713–4716.

LinkOut - more resources