Issue 5, 2015

A highly stereo-controlled protocol to prepare pipecolic acids based on Heck and cyclohydrocarbonylation reactions

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.

Graphical abstract: A highly stereo-controlled protocol to prepare pipecolic acids based on Heck and cyclohydrocarbonylation reactions

Supplementary files

Article information

Article type
Research Article
Submitted
20 jan 2015
Accepted
06 mar 2015
First published
09 mar 2015

Org. Chem. Front., 2015,2, 526-530

Author version available

A highly stereo-controlled protocol to prepare pipecolic acids based on Heck and cyclohydrocarbonylation reactions

G. Arena, E. Cini, E. Petricci, R. Randino and M. Taddei, Org. Chem. Front., 2015, 2, 526 DOI: 10.1039/C5QO00025D

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