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

作者:Arena Giada*; Cini Elena; Petricci Elena; Randino Rosario; Taddei Maurizio
来源:Organic Chemistry Frontiers, 2015, 2(5): 526-530.
DOI:10.1039/c5qo00025d

摘要

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 phenoneoxime 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.

  • 出版日期2015