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Enol ether structural motifs exist in many highly oxygenated biologically active natural products and pharmaceuticals. The synthesis of the geometrically less stable Z-enol ethers is challenging. An efficient Z-selective oxidative isomerization process of allyl ethers catalyzed by a cobalt­(II) (salen) complex using N-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate (Me3NFPY•OTf) as an oxidant has been developed. Thermodynamically less stable Z-enol ethers were prepared in excellent yields with high geometric control. This methodology also demonstrates the effectiveness in controlling the Z-selective isomerization reaction of diallyl ethers at room temperature. This catalytic system provides an alternative pathway to extend the traditional reductive isomerization of allyl ethers.

Our study aimed to assess the distribution of copper (Cu) in umbilical cord serum and estimated the association between umbilical serum Cu status and neonatal birth outcomes in a Chinese population. Through the Ma'anShan Birth Cohort Study, 2689 maternal-singleton pairs with detailed birth records and available serum samples were identified. The tertile levels of ln-transformed Cu were used to define low, medium, and high levels for serum Cu. The median for umbilical cord serum Cu was 298.2 μg/L with a range of 123.1-699.6 μg/L in this study population. Our study found a positive association between the concentration of serum Cu in the umbilical cord and the duration of gestation. Compared with medium Cu levels, we found that infants with low Cu levels had a significant higher risk of preterm birth (OR = 5.06, 95% CI 2.74, 9.34) and early-term birth (OR = 1.36, 95% CI 1.10, 1.69) in the crude model. We also found that infants with high Cu levels had a significant higher risk of late- or post-term birth (OR = 1.47, 95% CI 1.11, 1.95). A significant higher risk of preterm, early-term, and late- or post-term birth still remained, even after adjustment for potential confounding factors. Our findings suggested that both Cu deficiency and Cu overload had an adverse effect on neonatal birth outcomes.

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