Origin of regioselectivity in the reactions of nitronate and enolate ambident anions

…, K Yomogida, H Yamagishi, A Otsuki…

文献索引：Sakata, Tomomi; Seki, Natsuko; Yomogida, Kozue; Yamagishi, Hiroko; Otsuki, Akino; Inoh, Chie; Yamataka, Hiroshi Journal of Organic Chemistry, 2012 , vol. 77, # 23 p. 10738 - 10744

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被引用次数: 6

摘要

The reactions of nitronates of ring-substituted phenylnitromethanes and enolates of ring- substituted 1-phenyl-2-propanones with MeOBs gave exclusively the O-methylated and C- methylated products, respectively. DFT calculations suggested that two factors, namely, intrinsic barriers and metal-cation coordination, control the C/O selectivity. The kinetic preference for O-methylation in the reactions of nitronates arises from the intrinsic barriers, ...