Practical method for the absolute configuration assignment of tert/tert 1,2-diols using their complexes with Mo2(OAc)4.
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.
Górecki
Marcin
M
Institute of Organic Chemistry of the Polish Academy of Sciences, Kasprzaka 44, 01-224 Warsaw, Poland.
Jabłońska
Ewa
E
Kruszewska
Anna
A
Suszczyńska
Agata
A
Urbańczyk-Lipkowska
Zofia
Z
Gerards
Michael
M
Morzycki
Jacek W
JW
Szczepek
Wojciech J
WJ
Frelek
Jadwiga
J
D006018:Glycols / Q000737:chemistry*; D015394:Molecular Structure; D008982:Molybdenum; D009942:Organometallic Compounds; D013237:Stereoisomerism
D006018:Glycols; D009942:Organometallic Compounds; C437387:dimolybdenum tetraacetate; D008982:Molybdenum