Issue 23, 2016

The assignment of the configuration for α-hydroxy acid esters using a CEC strategy

Abstract

A simple and efficient 1H NMR method for determining the absolute configuration of chiral α-hydroxy acid esters using a competing enantioselective conversion (CEC) strategy was developed. The α-hydroxy acid esters were acylated in the presence of Feng's chiral N,N′-dioxide–scandium(III) complex, and the faster reaction was identified when one enantiomer of the chiral α-hydroxy acid ester was treated with both enantiomers of the ligand by NMR analysis of the reaction mixture without further purification. A mnemonic is presented to aid the assignment of the absolute configuration of the substrates.

Graphical abstract: The assignment of the configuration for α-hydroxy acid esters using a CEC strategy

Supplementary files

Article information

Article type
Paper
Submitted
29 Apr 2016
Accepted
10 May 2016
First published
18 May 2016

Org. Biomol. Chem., 2016,14, 5258-5262

The assignment of the configuration for α-hydroxy acid esters using a CEC strategy

R. Peng, L. Lin, Y. Zhang, W. Wu, Y. Lu, X. Liu and X. Feng, Org. Biomol. Chem., 2016, 14, 5258 DOI: 10.1039/C6OB00927A

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