Stereoselective synthesis of 3-hydroxyproline benzyl esters from N-protected beta-aminoaldehydes and benzyl diazoacetate |
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| Authors: | Angle Steven R Belanger Dominique S |
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| Institution: | Department of Chemistry, University of California-Riverside, Riverside, California 92521-0403, USA. steven.angle@ucr.edu |
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| Abstract: | 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. |
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