Stereoselective reduction of enantiopure α-l-amino-β-keto esters using oxazaborolidine catalysts for the synthesis of statine analogues
Year: 2025
Type: article
Abstract: An efficient diastereoselective synthesis of Boc-protected 4-amino 3-hydroxy esters starting from natural amino acids is described. The key synthetic strategy involves diastereoselective reduction of α-L-amino-β-keto esters in the presence of enantiopure R and S-2-Methyl-CBS-oxazaborolidine catalysts using borane as hydride source. The product diastereoselectivity depends upon the use of (R) or (S) enantiomer of 2-Methyl-CBS-oxazaborolidine. A reasonable mechanism is included which explains the diastereoselectivity of the reactions with the use of different enantiomers of 2-Methyl-CBS-oxazaborolidine. Furthermore, the resulting diastereomeric mixture of the reduced products can be separated by column chromatography to gain access to the single pure diastereomers.
Source: Organic Communications
Institution: Andhra University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: diamond
OpenAlex ID: W4411803180