(1<i>R</i>/<i>S</i>,7a<i>S</i>/<i>R</i>)-1-Benzyl-1-[2,8-bis(trifluoromethyl)quinolin-4-yl]-hexahydro-oxazolo[3,4-<i>a</i>]pyridin-3-one

Abstract

An unexpected diastereoselective C-alkylation of a mefloquine derivative in up to 57% yield was the result of an attempted Williamson etherification of Boc-mefloquine. The domino reaction involved oxazolidinone ring closure, deprotonation, and stereoselective carbon–carbon bond formation. The structure was confirmed with 2D NMR experiments.

Keywords

• mefloquine
• oxazolidinone
• C-alkylation
• diastereoselectivity