A one-pot, reductive amination/6-endo-trigcyclisation for the stereoselective synthesis of 6-substituted-4-oxopipecolic acids?

Chemical Communications Pub Date: 2011-05-13 DOI: 10.1039/C1CC11916H

Abstract

The first stereoselective synthesis of 2,6-trans-6-substituted-4-oxo-L-pipecolic acids using a tandem reductive amination/6-endo-trigcyclisation process is described. The sequential reduction and cyclisation mediated by sodium cyanoborohydride allowed the preparation of a series of highly functionalised 6-alkyl and 6-aryl analogues.

Graphical abstract: A one-pot, reductive amination/6-endo-trigcyclisation for the stereoselective synthesis of 6-substituted-4-oxopipecolic acids
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