Anti-Markovnikov alcohols via epoxide hydrogenation through cooperative catalysis

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Science  24 May 2019:
Vol. 364, Issue 6442, pp. 764-767
DOI: 10.1126/science.aaw3913

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Markovnikov falls to chromium and titanium

Ring opening of strained triangular epoxides is a versatile method for making alcohols. However, these reactions are limited by their tendency to leave the oxygen on the more heavily substituted carbon, in accord with the Markovnikov rule. Yao et al. now show that a pair of catalysts working cooperatively can invert this selectivity pattern. A titanium catalyst pries the ring open while a chromium catalyst activates and delivers hydrogen. In an unusual mechanistic twist, the chromium complex appears to deliver a hydrogen atom, a proton, and an electron at different stages of the cycle.

Science, this issue p. 764