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Stereoselective Synthesis of 3-Hydroxyproline Benzyl Esters from N-Protected β-Aminoaldehydes and Benzyl Diazoacetate

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journal contribution
posted on 25.06.2004, 00:00 by Steven R. Angle, Dominique S. Belanger
The synthesis of a series of 3-hydroxyproline benzyl esters from α-alkyl and α-alkoxy N-protected aminoaldehydes with benzyl diazoacetate is described. Aldehydes with α-alkyl substituents afforded prolines as a single diastereomer with a trans-cis relative configuration in 14−77%. An α-tert-butyldimethylsilyloxy aminoaldehyde afforded a proline as a single diastereomer with a trans-trans relative configuration in 37% yield.