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. 2012 Mar 7;134(9):4064-7.
doi: 10.1021/ja2119833. Epub 2012 Feb 22.

Highly diastereoselective synthesis of tetrahydropyridines by a C-H activation-cyclization-reduction cascade

Simon Duttwyler  1 , Colin Lu, Arnold L Rheingold, Robert G Bergman, Jonathan A Ellman
Affiliations

Highly diastereoselective synthesis of tetrahydropyridines by a C-H activation-cyclization-reduction cascade

Simon Duttwyler et al. J Am Chem Soc. .

Erratum in

  • J Am Chem Soc. 2014 Aug 20;136(33):11849

Abstract

A versatile reaction cascade leading to highly substituted 1,2,3,6-tetrahydropyridines has been developed. It comprises rhodium(I)-catalyzed C-H activation-alkyne coupling followed by electrocyclization and subsequent acid/borohydride-promoted reduction. This one-pot procedure affords the target compounds in up to 95% yield with >95% diastereomeric purity.

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Figures

Scheme 1
Scheme 1
Reaction Cascade for the One Pot, Stereoselective Synthesis of Piperidine Derivatives.
Scheme 2
Scheme 2
Proposed Mechanism for the Stereoselective Reduction and Ball-and-Stick Representation of [6e–H]+.
See this image and copyright information in PMC

References

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