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 Sep 3;11(17):3870-3.
doi: 10.1021/ol901314w.

Lanthanum tricyanide-catalyzed acyl silane-ketone benzoin additions

James C Tarr  1 , Jeffrey S Johnson
Affiliations

Lanthanum tricyanide-catalyzed acyl silane-ketone benzoin additions

James C Tarr et al. Org Lett. .

Abstract

Lanthanum tricyanide efficiently catalyzes a benzoin-type coupling between acyl silanes and ketones. Yields range from moderate to excellent over a broad substrate scope encompassing aryl, alkyl, electron-rich, and sterically hindered ketones.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Previous examples of aldehyde-ketone benzoin reactions.
Figure 2
Figure 2
Proposed acyl silane-ketone benzoin reaction
Figure 3
Figure 3
NOESY Analysis to Determine Equatorial Attack
See this image and copyright information in PMC

References

    1. Coppola GM, Schuster HF. α-Hydroxy Acids in Enantioselective Synthesis. Weinheim, Germany: Wiley-VCH; p. 1997.
    2. Hanessian S. Total Synthesis of Natural Products: The Chiron Approach. New York: Pergamon; 1983. Chapter 2.
    1. Lapworth A. J. Chem. Soc. 1903;83:995–1005.
    1. Enders D, Kalfass U. Angew. Chem. Int. Ed. 2002;41:1743–1745. references therein. - PubMed
    2. Dunkelmann P, Kolter-Jung D, Nitsche A, Demir AS, Siegert P, Lingen B, Baumann M, Pohl M, Muller M. J. Am. Chem. Soc. 2002;124:12084–12085. - PubMed
    3. Hachisu Y, Bode JW, Suzuki K. Adv. Synth. Catal. 2004;346:1097–1100.
    4. Enders D, Oliver N. Synlett. 2004:2111–2114.
    1. Linghu X, Potnick JR, Johnson JS. J. Am. Chem. Soc. 2004;126:3070–3071. - PubMed

    1. Deprotonation of silyl cyanohydrins: Bunnelle EM, Smith CR, Lee SK, Singaram SW, Rhodes AJ, Sarpong R. Tetrahedron. 2008;64:7008–7014. Wessig P, Glombitza C, Mueller G, Teubner J. J. Org. Chem. 2004;69:7582–7591. Lithiation of vinyl ethers: Palomo C, Oiarbide M, Arceo E, Garcia JM, Lopez R, Gonzalez A, Linden A. Angew. Chem. Int. Ed. 2005;44:6187–6190. Deprotonation of dithianes: Nicolaou KC, Magolda RL, Sipio WJ, Barnette WE, Lysenko Z, Joullie MM. J. Am. Chem. Soc. 1980;102:3784–3793.

Publication types

LinkOut - more resources