Preparation and use of hydantion-based chiral stationary phases

✍ Scribed by William H. Pirkle; Myung Ho Hyun

• Book ID: 104146628
• Publisher: Elsevier Science
• Year: 1985
• Tongue: English
• Weight: 856 KB
• Volume: 322
• Category: Article
• ISSN: 1873-3778
• DOI: 10.1016/s0021-9673(01)97690-3

✦ Synopsis

Starting from a-naphthyl Cpentenyl ketone, hydantoin-based chiral stationary phase 6a has been prepared. Chiral stationary phase 6a has proven to be quite effective for the separation of the enantiomers of hundreds of 3,Glinitrobenzamides derived from amino acids, amino esters, amino amides, amino phosphonates, amino alcohols and amines. A chiral recognition model involving three simultaneous stereochemically-dependent interactions is advanced to account for the observed elution orders of the enantiomers. On the basis of the chiral recognition model, a rational improvement was made in the design of the hydantoin chiral stationary phase. For example, enhancing the Ir-basicity of the naphthyl system [chiral stationary phase 6b, derived from (R)-5-(6,7-dimethyl-l-naphthyl)-5-(5-triethoxysilyl)hydantoin] has led to significantly improved performance relative to phase 6a, which lacks the 6,7-dimethyl groups. Ring-alkylated chiral stationary phase 6c has also been prepared and evaluated relative to phase 6a.