Hydroxy amines from halo alcohols

The application of antibiotics as chiral selectors has resulted in the successful resolution of almost all types of neutral, acidic, and basic racemic molecule. These antibiotics have been used for the enantiomeric resolution of amino acids, their derivatives, peptides, alcohols, and other pharmaceuticals. The selectivities of the most commonly used antibiotic-based (vancomycin, teicoplanin, and ristocetin A) CSPs varied from one racemate to another and are given in Table 1. Vancomycin was used for the chiral resolution of amino acids, amines, amides, imides, cyclic amines, amino alcohols, hydantoins, barbiturates, oxazolidinones, acids, profens, and other pharmaceuticals. Teicoplanin was found to be excellent chiral selector for the enantiomeric resolution of amino acids, amino alcohols, imides, peptides, hydantoins, a-hydroxy and halo acids, and oxazolidinones, whereas ristocetin A is capable of chiral resolution of amino acids, imides, amino... 

If the hydroxy group of a 2-amino alcohol is replaced by a mercapto group (XCIX) the reaction with carbon disulfide yields thiazolidine-2-thiones (C) with liberation of hydrogen sulfide. This method though is practically never used since thiazolidine-2-thiones are more simply obtained from 2-halo amines (see further under Section IV.l) which are themselves starting materials for the 2-amine thiols. 

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