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|Title:||A highly stereo-controlled protocol to prepare pipecolic acids based on Heck and cyclohydrocarbonylation reactions||Authors:||Arena, G. and Cini
and Petricci, Elena
and Randino, E.
and Taddei, R.
|Issue Date:||2015||Project:||None||Journal:||ORGANIC CHEMISTRY FRONTIERS||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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