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Paper | Regular issue | Vol 55, No. 2, 2001, pp.353-364
Published online, 1st January, 1970
DOI: 10.3987/COM-00-9114
A Three-Step Synthesis of Optically ActiveÅ@5-Halomethyl-2-oxazolidinones; Asymmetric Desymmetrization of Prochiral 1,3-Dihalo-2-propyl Carbamates

Shigeo Sugiyama, Kenji Morishita, and Keitaro Ishii*

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


Optically active 5-bromomethyl-2-oxazolidinones (2a and 3a) and 5-Å@chloromethyl-2-oxazolidinones (2b and 3b) were readily prepared from prochiral 1,3-dibromo-2-propanol (7a) and 1,3-dichloro-2-propanol (7b) by a three-step sequence involving formation of carbamates (6a-c) followed by asymmetric desymmetrization (up to 50% de) and debenzylation by anisole-methanesulfonic acid system.