A breakthrough in the asymmetric isomerization of 4,7-dihydro-1,3-dioxepins 1 was achieved by using DuPHOS-modified dihalogenonickel complexes such as 4 as catalyst precursors. The absolute configurations of the isomerization products were determined by transforming 2 into 2-hydroxy-γ-butyrolactone 3 and 1,2,4-butanetriol through a new oxidation-ring contraction sequence. The relative configuration of the oxidation product 5 was established by crystal structure analysis.
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Frauenrath et al. (2001) studied this question.
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