A novel synthetic protocol based on an indium-mediated glyoxylate allylation, Heck coupling and Rh-catalysed cyclohydrocarbonylation (CHC) was established to access enantiomerically pure polysubstituted pipecolic acids. The key steps are the Heck reaction, which is performed exclusively using a phenone-oxime derived palladacycle and the domino hydroformylation-cyclisation of a styryl derivative obtained from the Heck coupling. The reaction scheme, proceeding with good stereoselectivity, is also suitable for the preparation of substituted piperidine derivatives
Arena, G., Cini, E., Petricci, E., Randino, E., Taddei, M. (2015). A highly stereo-controlled protocol to prepare pipecolic acids based on Heck and cyclohydrocarbonylation reactions. ORGANIC CHEMISTRY FRONTIERS, 2(5), 526-530 [10.1039/c5qo00025d].
A highly stereo-controlled protocol to prepare pipecolic acids based on Heck and cyclohydrocarbonylation reactions
ARENA, GIADA;CINI, ELENA;PETRICCI, ELENA;TADDEI, MAURIZIO
2015-01-01
Abstract
A novel synthetic protocol based on an indium-mediated glyoxylate allylation, Heck coupling and Rh-catalysed cyclohydrocarbonylation (CHC) was established to access enantiomerically pure polysubstituted pipecolic acids. The key steps are the Heck reaction, which is performed exclusively using a phenone-oxime derived palladacycle and the domino hydroformylation-cyclisation of a styryl derivative obtained from the Heck coupling. The reaction scheme, proceeding with good stereoselectivity, is also suitable for the preparation of substituted piperidine derivatives
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https://hdl.handle.net/11365/982103
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