Diastereoselective Synthesis of γ-Phthalimido-β-Hydroxy Esters and N-Protected 4-Amino-1,3-Diols Starting from Natural α-Amino Acids

Title: Diastereoselective Synthesis of γ-Phthalimido-β-Hydroxy Esters and N-Protected 4-Amino-1,3-Diols Starting from Natural α-Amino Acids

Volume: 7 Issue: 1

Author(s): Amel Essersi, Ridha Touati and Bechir Ben Hassine

Affiliation:

Keywords: Amino acids, phthalimide analogues, chiral -β-keto esters, amino acid derivatives, β-hydroxy esters, N-protected 4-amino-1, 3-diols

Abstract: An efficient diastereoselective synthes.is of γ-phthalimido-β-hydroxy esters and N-protected 4-amino-1,3- diols, starting from natural amino acids is described. The key synthetic strategies involve diastereoselective reduction of γ-phthalimido-β-keto esters with NaBH4 as hydride reducing. The diastereoselective reduction has been found to be highly selective if carried out in methanol at -78°C. Furthermore, the resulting diastereomeric mixture of the reduced products was successfully and cleanly separated by column chromatography.

Cite this article as:

Essersi Amel, Touati Ridha and Hassine Ben Bechir, Diastereoselective Synthesis of γ-Phthalimido-β-Hydroxy Esters and N-Protected 4-Amino-1,3-Diols Starting from Natural α-Amino Acids, Letters in Organic Chemistry 2010; 7 (1) . https://dx.doi.org/10.2174/157017810790533869