Just when you thought it was safe to assume . . .

One thing we were all taught (and some of us teach) is that Sn2 reactions don’t occur at tertiary carbons. Ionization comes first with loss of stereochemistry followed by either sided attack on the carbonium ion (pardon my French). Well along comes Nature vol. 501 pp. 195 – 199 ’13 with a Sn2 reaction on a tertiary carbon, complete with inversion of stereochemistry, using a nitrogen containing nucleophile (and a Lewis acid). Even more counterintuitive is that the reaction is selective for tertiary carbons leaving primary and secondary carbons alone. Certain to be of use to the medicinal chemist. It’s already been used to prepare marine terpenoids from terrestrial terpenoid precursors.

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