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  • A one-pot, reductive amination/6-endo-trig cyclisation for the stereoselective synthesis of 6-substituted-4-oxopipecolic acids.

A one-pot, reductive amination/6-endo-trig cyclisation for the stereoselective synthesis of 6-substituted-4-oxopipecolic acids.

Chemical communications (Cambridge, England) (2011-05-17)
Lindsay S Fowler, Lynne H Thomas, David Ellis, Andrew Sutherland
ABSTRACT

The first stereoselective synthesis of 2,6-trans-6-substituted-4-oxo-L-pipecolic acids using a tandem reductive amination/6-endo-trig cyclisation 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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Pipecolinic acid, 98%
Sigma-Aldrich
Sodium cyanoborohydride solution, 1.0 M in THF
Sigma-Aldrich
Sodium cyanoborohydride solution, 5.0 M in 1 M NaOH
Sigma-Aldrich
Sodium cyanoborohydride, reagent grade, 95%
Sigma-Aldrich
L-Pipecolic acid, 99% (titration)