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Paper | Regular issue | Vol 57, No. 4, 2002, pp.637-648
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9429
Chemoselective Debezylation of the N-1-Phenylethyl Goup in 2-Oxazolidinones by the Anisole-Methanesulfonic Acid System

Shigeo Sugiyama, Kenji Morishita, Mariko Chiba, and Keitaro Ishii*

*Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan


The chemoselective removal of N-1-phenylethyl group in 2-oxazolidinones by the anisole–methanesulfonic acid system was investigated. Optically active 4,5-cis- and 4,5-trans-diphenyl-2-oxazolidinones (1a–d) were easily synthesized from dl-stilbene oxides (trans- and cis-7a) using this debenzylation.