Practical Method for the Absolute Configuration Assignment of tert/tert 1,2-Diols Using Their Complexes with Mo2(OAc)4
The Journal of Organic Chemistry2007Vol. 72(8), pp. 2906–2916
Citations Over TimeTop 18% of 2007 papers
Marcin Górecki, Ewa Jabłońska, Anna Kruszewska, Agata Suszczyńska, Z. Urbańczyk-Lipkowska, M. Gerards, Jacek W. Morzycki, Wojciech J. Szczepek, Jadwiga Frelek
Abstract
We describe here an application of the practical, simple, and reliable approach for the determination of the absolute configuration of sterically demanding tert/tert vic-diols. According to this method, it is only necessary to mix dimolybdenum tetraacteate and a chiral diol in DMSO and record the CD spectra in the 250-650 nm spectral range. From the sign of the CD bands occurring at around 310, 350, and 400 nm, it is possible to establish the chirality of the diol unit expressed by the sign of the O-C-C-O torsion angle. Because the preferred conformation of the diol in the formed complex is known, we are able to determine the absolute configuration of the carbon atoms in the diol subunit even in flexible tert/tert vic-diols.
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