Regiocontrolled Construction of Functionalized Spiro[4.4]Nonanones Through Mercury(II) Salt-Assisted and Acid-Induced Spiroannulation Reactions

Yoshinobu Hashizume Department of Applied Physics and Chemistry, The University of Electro-Communications, Chofu, Tokyo, 182-8585, Japan

Shojiro Maki Department of Applied Physics and Chemistry, The University of Electro-Communications, Chofu, Tokyo, 182-8585, Japan

Mamoru Ohashi Department of Applied Physics and Chemistry, The University of Electro-Communications, Chofu, Tokyo, 182-8585, Japan

Haruki Niwa Department of Applied Physics and Chemistry, The University of Electro-Communications, Chofu, Tokyo, 182-8585, Japan

Abstract

The mercuric(II)-assisted spiroannulation reactions of the enol silyl ethers derived from α-(4-pentynyl)-cyclopentanones 8a and 11 gave functionalized spiro[4.4]nonanones, exo-3 and exo-4 respectively, in moderate yields. On the other hand, the treatment of 8a and 8b with methanesulfonic acid provided endo-3 in high yield.

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Regiocontrolled Construction of Functionalized Spiro[4.4]Nonanones Through Mercury(II) Salt-Assisted and Acid-Induced Spiroannulation Reactions

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Regiocontrolled Construction of Functionalized Spiro[4.4]Nonanones Through Mercury(II) Salt-Assisted and Acid-Induced Spiroannulation Reactions

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