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Synthesis 1993; 1993(3): 307-310
DOI: 10.1055/s-1993-25854
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Lewis Acid Mediated Cyclization of Epoxy Benzoylcarbamates

Makoto Yamamoto* , Makoto Suzuki, Keiki Kishikawa, Shigeo Kohmoto
  • *Department of Materials Science, Faculty of Engineering, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba-shi, 263, Japan
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Publication Date:
17 September 2002 (online)

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Lewis acid mediated cyclization of 2,3-epoxypropylbenzoylcarbamates is described. trans-Aryl-substituted epoxy carbamates cyclized to 4-(α-benzoylbenzyl)-1,3-dioxolan-2-ones and 4-aryl-3-benzoyl-5-hydroxymethyloxazolidin-2-ones. On the contrary, cis-aryl- and alkyl-substituted epoxy carbamates gave only 4-[1-(benz-oyloxy)alkyl]oxazolidin-2-ones. Mechanism of this cyclization is also discussed.

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