Stereoselective synthesis of 3-hydroxyproline benzyl esters from N-protected beta-aminoaldehydes and benzyl diazoacetate.
The synthesis of a series of 3-hydroxyproline benzyl esters from alpha-alkyl and alpha-alkoxy N-protected aminoaldehydes with benzyl diazoacetate is described. Aldehydes with alpha-alkyl substituents afforded prolines as a single diastereomer with a trans-cis relative configuration in 14-77%. An alpha-tert-butyldimethylsilyloxy aminoaldehyde afforded a proline as a single diastereomer with a trans-trans relative configuration in 37% yield.
Angle
Steven R
SR
Department of Chemistry, University of California-Riverside, Riverside, California 92521-0403, USA. steven.angle@ucr.edu
Belanger
Dominique S
DS