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

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.

SUBMITTER: Duttwyler S 

PROVIDER: S-EPMC3319108 | biostudies-literature | 2012 Mar

REPOSITORIES: biostudies-literature

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

Duttwyler Simon S   Lu Colin C   Rheingold Arnold L AL   Bergman Robert G RG   Ellman Jonathan A JA  

Journal of the American Chemical Society 20120222 9

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. ...[more]

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