Functionalization of Piperidine Derivatives for the Site‐Selective and Stereoselective Synthesis of Positional Analogues of Methylphenidate
Year: 2019
Type: article
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 Rh2(R‐TCPTAD)4, or N‐brosyl‐piperidine using Rh2(R‐TPPTTL)4 generated 2‐substitited analogues. In contrast, when N‐α‐oxoarylacetyl‐piperidines were used in combination with Rh2(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.
Source: Chemistry - A European Journal
Institutions: Emory University, University of Regensburg
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,000
Awards: G1871608568, G2027168600, New Directions in Enantioselective C-H Functionalization, G227176262, G236029928, MRI: Acquisition of a 600 MHz NMR Spectrometer for Chemistry, G3085896116, MRI: Acquisition of a High Intensity Single Crystal X-ray Diffractometer, G4421890870, G454325550, G731485014, NSF Center for Selective CH Functionalization
OpenAlex ID: W2997650997