Liu, Wenbin and Babl, Tobias and Roether, Alexander and Reiser, Oliver and Davies, Huw M. L. (2020) Functionalization of Piperidine Derivatives for the Site-Selective and Stereoselective Synthesis of Positional Analogues of Methylphenidate. CHEMISTRY-A EUROPEAN JOURNAL, 26 (19). pp. 4236-4241. ISSN 0947-6539, 1521-3765
Full text not available from this repository. (Request a copy)Abstract
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 N-Boc-piperidine using Rh-2(R-TCPTAD)(4), or N-brosyl-piperidine using Rh-2(R-TPPTTL)(4) generated 2-substitited analogues. In contrast, when N-alpha-oxoarylacetyl-piperidines were used in combination with Rh-2(S-2-Cl-5-BrTPCP)(4), the C-H functionalization produced 4-susbstiuted analogues. Finally, the 3-substituted analogues were prepared indirectly by cyclopropanation of N-Boc-tetrahydropyridine followed by reductive regio- and stereoselective ring-opening of the cyclopropanes.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | H BOND FUNCTIONALIZATION; ACTIVATION; ARYLDIAZOACETATES; DIVERSIFICATION; HYDROXYLATION; NITROGEN; PROLINE; ENABLES; ALPHA; TOOLS; C-H functionalization; diastereoselectivity; piperidines; regioselectivity; rhodium |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 29 Mar 2021 06:56 |
| Last Modified: | 29 Mar 2021 06:56 |
| URI: | https://pred.uni-regensburg.de/id/eprint/44852 |
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