Malcolm Spain

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The mechanism of the SmI2 -mediated reduction of unactivated esters has been studied using a combination of kinetic, radical clocks and reactivity experiments. The kinetic data indicate that all reaction components (SmI2 , amine, H2 O) are involved in the rate equation and that electron transfer is facilitated by Brønsted base assisted deprotonation of(More)
Highly chemoselective direct reduction of primary, secondary, and tertiary amides to alcohols using SmI2/amine/H2O is reported. The reaction proceeds with C-N bond cleavage in the carbinolamine intermediate, shows excellent functional group tolerance, and delivers the alcohol products in very high yields. The expected C-O cleavage products are not formed(More)
Since the 1864 landmark discovery by Adolf von Baeyer, [1] barbituric acids have played a prominent role in medicine and organic synthesis. The barbituric acid scaffold occurs in more than 5000 pharmacologically active compounds, including commonly used anticonvulsant, hypnotic, and anticancer agents (Figure 1 a). [2] Moreover, as an easily accessible(More)
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