Functionalization of Piperidine Derivatives for the Site‐Selective and Stereoselective Synthesis of Positional Analogues of Methylphenidate

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  • Wenbin Liu
    Department of Chemistry Emory University 1515 Dickey Drive Atlanta GA 30322 USA
  • Tobias Babl
    Department of Chemistry Emory University 1515 Dickey Drive Atlanta GA 30322 USA
  • Alexander Röther
    Institute of Organic Chemistry, University of Regensburg Universitätsstrasse 31 93053 Regensburg Germany
  • Oliver Reiser
    Institute of Organic Chemistry, University of Regensburg Universitätsstrasse 31 93053 Regensburg Germany
  • Huw M. L. Davies
    Department of Chemistry Emory University 1515 Dickey Drive Atlanta GA 30322 USA

書誌事項

公開日
2020-03-09
権利情報
  • http://creativecommons.org/licenses/by-nc-nd/4.0/
DOI
  • 10.1002/chem.201905773
公開者
Wiley

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説明

<jats:title>Abstract</jats:title><jats:p>Rhodium‐catalyzed C−H insertions and cyclopropanations of donor/acceptor carbenes have been used for the synthesis of positional analogues of methylphenidate. The site selectivity is controlled by the catalyst and the amine protecting group. C−H functionalization of <jats:italic>N</jats:italic>‐Boc‐piperidine using Rh<jats:sub>2</jats:sub>(<jats:italic>R</jats:italic>‐TCPTAD)<jats:sub>4</jats:sub>, or <jats:italic>N</jats:italic>‐brosyl‐piperidine using Rh<jats:sub>2</jats:sub>(<jats:italic>R</jats:italic>‐TPPTTL)<jats:sub>4</jats:sub> generated 2‐substitited analogues. In contrast, when <jats:italic>N</jats:italic>‐α‐oxoarylacetyl‐piperidines were used in combination with Rh<jats:sub>2</jats:sub>(<jats:italic>S</jats:italic>‐2‐Cl‐5‐BrTPCP)<jats:sub>4</jats:sub>, the C−H functionalization produced 4‐susbstiuted analogues. Finally, the 3‐substituted analogues were prepared indirectly by cyclopropanation of <jats:italic>N</jats:italic>‐Boc‐tetrahydropyridine followed by reductive regio‐ and stereoselective ring‐opening of the cyclopropanes.</jats:p>

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