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

• Published in: Chemical & pharmaceutical bulletin Vol. 43; no. 4; pp. 708 - 710
• Main Authors: YAMASHITA, M, OKUYAMA, K, OHHARA, T, KAWASAKI, OHTA, S
• Format: Journal Article
• Language: English
• 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

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.