RING-OPENING OF CYCLOPROPANECARBOXYLATES USING SAMARIUM(II) DIIODIDE (SMI2)-HMPA-THF SYSTEM

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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Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 43; no. 4; pp. 708 - 710
Main Authors YAMASHITA, M, OKUYAMA, K, OHHARA, T, KAWASAKI, OHTA, S
Format Journal Article
LanguageEnglish
Published TOKYO Pharmaceutical Soc Japan 1995
Maruzen
Subjects
Aliphatic compounds
Chemistry
Chemistry, Medicinal
Chemistry, Multidisciplinary
Exact sciences and technology
Life Sciences & Biomedicine
Organic chemistry
Pharmacology & Pharmacy
Physical Sciences
Preparations and properties
Science & Technology
CYCLOPROPANE
SAMARIUM DIIODIDE
ORGANIC-SYNTHESIS
SMI2
4-ARYL-3-TRIMETHYLSILYLBUTYRATE
RING OPENING
4-ARYLBUTYRATE
CARBONYL-COMPOUNDS
DERIVATIVES
CYCLOPROPANECARBOXYLATE
Regioselectivity
Aliphatic compound
Samarium II Iodides
Hexamethylphosphorotriamide
Tetrahydrofurane
Monocyclic compound
Ring cleavage
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Summary: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.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.43.708