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

• Published in: Journal of organic chemistry Vol. 69; no. 13; pp. 4361 - 4368
• Main Authors: Angle, Steven R, Belanger, Dominique S
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 25.06.2004; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; PROLINE DERIVATIVES; ASYMMETRIC-SYNTHESIS; SUBSTITUTED PROLINES; TETRAHYDROFURANS; AZOMETHINE YLIDES; EFFICIENT SYNTHESIS; ALPHA-AMINO-ACIDS; ALDEHYDES; 1,3-DIPOLAR CYCLOADDITION REACTIONS; ETHYL DIAZOACETATE; Stereoselectivity; Ester; Aminoaldehyde; Benzylic compound; Nitrogen heterocycle; Aminoacid; Relative configuration; Organic siloxane; Chemical synthesis; Protection; Diastereomer
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo030360f

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.