Use of osmate(VI) ester trans-N,N,N′ ,N′-tetramethyl-1,2-cyclohexanediamine complexes for determination of glycol stereochemistry

✍ Scribed by James F. Resch; Jerrold Meinwald

• Book ID: 104234184
• Publisher: Elsevier Science
• Year: 1981
• Tongue: French
• Weight: 228 KB
• Volume: 22
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)81852-9

✦ Synopsis

Osmate(VI) esters chelated with optically active trans-N,N,N',N'-tetramethyl-1,2-cyclohexanediamine are useful derivatives for enantiomeric identification of sub-milligram quantltles of glycols by 1 H NMR spectroscopy. The recognition or determination of the chirality of vicinal glycols has received consxderable attention, in part as a consequence of the importance of this functionality in natural products chemistry. Derivatization with chiral acyl halides' or isocyanates, 2 useful with primary and secondary alcohols, becomes a more complex process with hindered alcohols or with glycols which may react to give mixtures of singly and doubly derivatized products. Chlroptical methods requiring no explicit substrate derivatization have also been developed. * Chemical shafts are in ppm downfleld tram rnternal Me4Sr for 0.1 acetone-d6. ** enantiomerrc osmate complex actually observed N-Me -4 2.64 2.66 4 _M solutions In