Literature DB >> 22356093

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

Simon Duttwyler1, Colin Lu, Arnold L Rheingold, Robert G Bergman, Jonathan A Ellman.   

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.
© 2012 American Chemical Society

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Year:  2012        PMID： 22356093      PMCID： PMC3319108          DOI： 10.1021/ja2119833

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  48 in total

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3.  Applications of CeCl(3) as an environmental friendly promoter in organic chemistry.

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5.  Oxidative coupling of aromatic substrates with alkynes and alkenes under rhodium catalysis.

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Journal:  Chemistry       Date:  2010-10-04       Impact factor: 5.236

Review 6.  Towards mild metal-catalyzed C-H bond activation.

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Review 7.  The chemistry and pharmacology of tetrahydropyridines.

Authors:  N N Mateeva; L L Winfield; K K Redda
Journal:  Curr Med Chem       Date:  2005       Impact factor: 4.530

8.  The vinyl moiety as a handle for regiocontrol in the preparation of unsymmetrical 2,3-aliphatic-substituted indoles and pyrroles.

Authors:  Malcolm P Huestis; Lina Chan; David R Stuart; Keith Fagnou
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9.  Stereoselective synthesis of 2,3,6-trisubstituted tetrahydropyridines via Tf(2)O-mediated Grob fragmentation: access to indolizidines (-)-209I and (-)-223J.

Authors:  Gérald Lemonnier; André B Charette
Journal:  J Org Chem       Date:  2010-11-05       Impact factor: 4.354

10.  Palladium(0)-catalyzed alkynyl and allenyl iminium ion cyclizations leading to 1,4-disubstituted 1,2,3,6-tetrahydropyridines.

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  21 in total

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3.  New Regio- and Stereoselective Cascades via Unstabilized Azomethine Ylide Cycloadditions for the Synthesis of Highly Substituted Tropane and Indolizidine Frameworks.

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Journal:  Angew Chem Int Ed Engl       Date:  2014-03-06       Impact factor: 15.336

5.  Synthesis of ent-ketorfanol via a C-H alkenylation/torquoselective 6π electrocyclization cascade.

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Journal:  Angew Chem Int Ed Engl       Date:  2015-08-17       Impact factor: 15.336

6.  Highly Diastereoselective Functionalization of Piperidines by Photoredox-Catalyzed α-Amino C-H Arylation and Epimerization.

Authors:  Morgan M Walker; Brian Koronkiewicz; Shuming Chen; K N Houk; James M Mayer; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2020-04-24       Impact factor: 15.419

7.  Synthesis of isoquinuclidines from highly substituted dihydropyridines via the Diels-Alder reaction.

Authors:  Rhia M Martin; Robert G Bergman; Jonathan A Ellman
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8.  Rapid Construction of (-)-Paroxetine and (-)-Femoxetine via N-Heterocyclic Carbene Catalyzed Homoenolate Addition to Nitroalkenes.

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9.  A catalytic asymmetric synthesis of polysubstituted piperidines using a rhodium(I)-catalyzed [2+2+2] cycloaddition employing a cleavable tether.

Authors:  Timothy J Martin; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2013-04-19       Impact factor: 15.336

10.  Unstabilized azomethine ylides for the stereoselective synthesis of substituted piperidines, tropanes, and azabicyclo[3.1.0] systems.

Authors:  Michael A Ischay; Michael K Takase; Robert G Bergman; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2013-02-11       Impact factor: 15.419
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