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. 2004 Apr 13;101(15):5472-5.
doi: 10.1073/pnas.0307556101. Epub 2004 Mar 15.

Catalytic asymmetric reactions for organic synthesis: the combined C-H activation/Cope rearrangement

Huw M L Davies  1 , Qihui Jin
Affiliations

Catalytic asymmetric reactions for organic synthesis: the combined C-H activation/Cope rearrangement

Huw M L Davies et al. Proc Natl Acad Sci U S A. .

Abstract

The development of new catalytic asymmetric reactions can lead to exciting new strategies for organic synthesis. This article describes the synthetic utility of the combined C-H activation/Cope rearrangement, achieved by dirhodium tetraprolinate-catalyzed reaction of vinyldiazoacetates with compounds containing allylic C-H bonds. The transformation is highly diastereoselective and enantioselective. The product distribution, however, is highly substrate dependent, the major side products being either direct C-H activation or cyclopropanation.

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Figures

Figure 1
Figure 1
In these equations, de indicates diastereomeric excess and ee indicates enantiomeric excess.
Scheme 1.
Scheme 1.
Scheme 2.
Scheme 2.
Scheme 3.
Scheme 3.
See this image and copyright information in PMC

References

    1. Jacobsen, E. N., Pfaltz, A. & Yamamoto, H., eds. (1999) Comprehensive Asymmetric Catalysis (Springer, Berlin), Vols. I–III.
    1. Ojima, I. (2000) Catalytic Asymmetric Synthesis (Wiley, New York), 2nd Ed.
    1. Jacobsen, E. N., Pfaltz, A. & Yamamoto, H. eds. (2003) Comprehensive Asymmetric Catalysis (Springer, Berlin), Suppl. 1.
    1. Davies, H. M. L. (1998) Curr. Org. Chem. 2, 463–488.
    1. Davies, H. M. L. & Antoulinakis, E. G. (2001) Org. Reactions 57, 1–326.

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