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Synlett 1995; 1995(6): 635-638
DOI: 10.1055/s-1995-5040
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Convenient Synthesis of Phthalides via Regioselective Baeyer-Villiger Oxidation of Benzocyclobutenones

Takamitsu Hosoya, Yokusu Kuriyama, Keisuke Suzuki*
  • *Department of Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223, Japan
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Publication Date:
31 December 2000 (online)

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The Baeyer-Villiger oxidation of benzocyclobutenones proceeds with rigorous regioselectivity to give phthalides in high yields. Coupled with the ready availability of benzocyclobutenones via [2+2] cycloaddition of benzyne and ketene silyl acetal, the present process provides an efficient entry into various phthalides. A short-step synthesis of iso-ochracinic acid demonstrates the efficiency of this process.

Phthalide - Baeyer-Villiger Oxidation - [2+2] Cycloaddition - Benzocyclobutenone - Regioselectivity