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. 2013 Aug 14;135(32):11756-9.
doi: 10.1021/ja406356c. Epub 2013 Aug 5.

Enantioselective α-alkenylation of aldehydes with boronic acids via the synergistic combination of copper(II) and amine catalysis

Jason M Stevens  1 , David W C MacMillan
Affiliations

Enantioselective α-alkenylation of aldehydes with boronic acids via the synergistic combination of copper(II) and amine catalysis

Jason M Stevens et al. J Am Chem Soc. .

Abstract

The enantioselective α-alkenylation of aldehydes has been accomplished using boronic acids via the synergistic combination of copper and chiral amine catalysis. The merger of two highly utilized and robust catalytic systems has allowed for the development of a mild and operationally trivial protocol for the direct formation of α-formyl olefins employing common building blocks for organic synthesis.

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Figures

Scheme 1
Scheme 1
Proposed Mechanism for Aldehyde α-Alkenylation.
Scheme 2
Scheme 2
Synergistic Catalysis Enabled Synthesis of Complex Structures from Commercially Available Building Blocks.
See this image and copyright information in PMC

References

    1. For a review on synergistic catalysis, see: Allen AE, MacMillan DWC. Chem Sci. 2012;3:633.For reviews on dual catalysis, see: Shao Z, Zhang H. Chem Soc Rev. 2009;38:2745.Zhong C, Shi X. Eur J Org Chem. 2010:2999.Patil NT, Shinde VS, Gajula B. Org Biomol Chem. 2012;10:211.

    1. Allen AE, MacMillan DWC. J Am Chem Soc. 2010;132:4986. - PMC - PubMed
    1. Allen AE, MacMillan DWC. J Am Chem Soc. 2011;133:4260. - PMC - PubMed
    1. Skucas E, MacMillan DWC. J Am Chem Soc. 2012;134:9090. - PMC - PubMed
    1. Simonovich SP, Van Humbeck JF, MacMillan DWC. Chem Sci. 2012;3:58. - PMC - PubMed

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