Discrimination of enantiomers of amides with two stereogenic centers enabled by chiral bisthiourea derivatives using ¹H NMR spectroscopy.

ABSTRACT: Enantiomers of a few new amides containing two stereogenic centers have been derived from d- and l-α-amino acids as guests for chiral recognition by 1H NMR spectroscopy. A variety of chiral amides with two or more stereogenic centers often exist in the products of catalytic asymmetric synthesis, natural products or their total synthetic products, and chiral drugs. It would be a challenging and meaningful work to explore their chiral recognition. For this purpose, a class of novel chiral bisthiourea derivatives 1-9 has been synthesized from (1S,2S)-(+)-1,2-diaminocyclohexane, d-α-amino acids, and isothiocyanates as chiral solvating agents (CSAs). CSAs 1-9 proved to afford better chiral discriminating results towards most amides with two stereogenic centers, which have been rarely studied as

SUBMITTER: Zhang H 

PROVIDER: S-EPMC9420356 | biostudies-literature | 2021 Aug

REPOSITORIES: biostudies-literature