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. 2011 Jul 13;133(27):10352-5.
doi: 10.1021/ja202969z. Epub 2011 Jun 20.

Catalytic asymmetric C-H insertions of rhodium(II) azavinyl carbenes

Stepan Chuprakov  1 , Jamal A Malik, Mikhail Zibinsky, Valery V Fokin
Affiliations

Catalytic asymmetric C-H insertions of rhodium(II) azavinyl carbenes

Stepan Chuprakov et al. J Am Chem Soc. .

Abstract

A highly efficient enantioselective C-H insertion of azavinyl carbenes into unactivated alkanes has been developed. These transition metal carbenes are directly generated from readily available and stable 1-sulfonyl-1,2,3-triazoles in the presence of chiral Rh(II) carboxylates and are used for C-H functionalization of alkanes to access a variety of β-chiral sulfonamides.

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Figures

Figure 1
Figure 1
Chiral Rh(II) carboxylates used in this study.
See this image and copyright information in PMC

References

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    1. Similarly to the previously reported Rh-catalyzed C–H insertion with diazoesters, dry and degassed solvents were used to ensure efficiency of the reaction. See Supporting Information for details. See also ref. 2b.

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