RING OPENING OF CYCLOPROPANECARBOXYLATES USING SAMURIUM(II) DIIODIDE (SmI2)-HMPA-THF SYSTEM

Masayuki YAMASHITA; Kazunori OKUYAMA; Takashi OHHARA; Ikuo KAWASAKI; Shunsaku OHTA

doi:10.1248/cpb.43.708

Chemical and Pharmaceutical Bulletin

Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363

RING OPENING OF CYCLOPROPANECARBOXYLATES USING SAMURIUM(II) DIIODIDE (SmI₂)-HMPA-THF SYSTEM

Masayuki YAMASHITA, Kazunori OKUYAMA, Takashi OHHARA, Ikuo KAWASAKI, Shunsaku OHTA

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Keywords: samurium diiodide, cyclopropane, ring opening, cyclopropanecarboxylate, 4-arylbutyrate, 4-aryl-3-trimethylsilylbutyrate

JOURNAL FREE ACCESS

1995 Volume 43 Issue 4 Pages 708-710

DOI https://doi.org/10.1248/cpb.43.708

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Abstract

Cyclopropane ring of 2- and 2, 3-substituted cyclopropanecarboxylates (1) was regioselectively cleaved using SmI₂-HMPA-THF system in the presence of tert-BuOH to give 4- and 3, 4-substituted butyrates (2) in moderate to good yields.

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