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
. 2011 Mar 4;13(5):995-7.
doi: 10.1021/ol102982b. Epub 2011 Feb 2.

Catalytic enantioselective conjugate allylation of unsaturated methylidene ketones

Laura A Brozek  1 , Joshua D Sieber, James P Morken
Affiliations

Catalytic enantioselective conjugate allylation of unsaturated methylidene ketones

Laura A Brozek et al. Org Lett. .

Abstract

The use of unsaturated methylidene ketones in catalytic conjugate allylations allows a significant expansion in substrate scope and, with appropriate chiral ligands, occurs in a highly enantioselective fashion.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1
Scheme 2
Scheme 2
Enantioselective Conjugate Allylation of 3 with Diastereoisomeric Ligands.
Scheme 3
Scheme 3
Synthesis of Cyclohexenone 11.
See this image and copyright information in PMC

References

    1. Reviews: (a) Krause N, Hoffmann-Röder A. Synthesis. 2001:171.Christoffers J, Koripelly G, Rosiak A, Rössle M. Synthesis. 2007:1279.Alexakis A, Bäckvall JE, Krause N, Pàimes O, Diéguez M. Chem Rev. 2008;108:2796.Harutyunyan SR, den Hartog T, Geurts K, Minnard AJ, Feringa BL. Chem Rev. 2008;108:2824.Hawner C, Alexakis A. Chem Commun. 2010;46:7295.

    1. Sieber JD, Liu S, Morken JP. J Am Chem Soc. 2007;129:2214.Sieber JD, Morken JP. J Am Chem Soc. 2008;130:4978.For a related process, see: Zhang P, Morken JP. J Am Chem Soc. 2009;131:12550.

    1. Méndez M, Cuerva JM, Gómez-Bengoa E, Cárdenas DJ, Echavarren AM. Chem Eur J. 2002;8:3620. - PubMed
    2. Cárdenas DJ, Echavarren AM. New J Chem. 2004;28:338.

    1. For other catalytic reactions that appear to proceed by 3,3′ reductive elimination, see: Keith JA, Behenna DC, Mohr JT, Ma S, Marinescu SC, Oxgaard J, Stoltz BM, Goddard WA., III J Am Chem Soc. 2007;129:11876.Bao M, Nakamura H, Yamamoto Y. J Am Chem Soc. 2001;123:759.Lu S, Xu Z, Bao M, Yamamoto Y. Angew Chem Int Ed. 2008;47:4366.Ariafard A, Lin Z. J Am Chem Soc. 2006;128:13010.

    1. For another catalytic enantioselective conjugate allylation, see: Shizuka M, Snapper ML. Angew Chem Int Ed. 2008;47:5049.For non-enantioselective catalytic version, see: Shaghafi MB, Kohn BL, Jarvo ER. Org Lett. 2008;10:4743.

Publication types