Determination of absolute configuration of acyclic 1,2-diols with Mo2(OAc)4. 1. Snatzke's method revisited.
The method employing dimolybdenum tetraacetate for the assignment of the absolute configuration of optically active 1,2-diols is thoroughly revisited and applied to several compounds, some of which were synthesized by asymmetric cis-dihydroxylation. No exceptions were found to the empirical rule relating the sign of the induced CD spectrum and the configuration of the substrate, whatever its structure and sterical requirements. To broaden the scope of the method, its applicability to critical situations commonly encountered with synthetic products is tested. It is demonstrated that the method can be applied on samples with low chemical and optical purity, and that it may lend itself as a means to estimate the ee. The roles of the water content of the sample and of the diol-to-dimolybdenum ratio are investigated.
Di Bari
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Centro di Studio del CNR per le Macromolecole Stereordinate e Otticamente Attive, Dipartimento di Chimica e Chimica Industriale, Università degli Studi di Pisa, via Risorgimento 35, I-56126 Pisa, Italy.
Pescitelli
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G
Pratelli
C
C
Pini
D
D
Salvadori
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P
D002942:Circular Dichroism; D006018:Glycols / Q000737:chemistry*; D008982:Molybdenum; D009942:Organometallic Compounds; D013237:Stereoisomerism
D006018:Glycols; D009942:Organometallic Compounds; C437387:dimolybdenum tetraacetate; D008982:Molybdenum