Asymmetric Syntheses of All Stereoisomers of 3-Hydroxyproline; A Constituent of Several Bioactive Compounds

Abstract

Synthesis of an unusual β-hydroxy-α-amino acid, 3-hydroxyproline, and its derivatives have been achieved enantioselectively by employing Sharpless asymmetric epoxidation and reductive cyclization as the key steps.

Key words

amino acid - Sharpless asymmetric epoxidation - azido epoxide - reductive cyclization - 3-hydroxyproline

• References and Notes

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This cyclization is according to Baldwin’s rules for ring closures, a formally disfavored process. However, Hevko et al. have reported a similar epoxide-opening reaction under basic conditions, where the product of the 5-endo-cyclization is preferred over that from a 4-exo process:
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