Lewis Acid-mediated Highly Regioselective Ring-expansion of Methyl 2-Phenyl-1-(arylhydroxymethyl)cyclopropanecarboxylates

• DOI: 10.1246/cl.2010.194
• Publication Date: 2010-02-01T06:13:14Z
• Authors: Eri Yoshida; Kazufumi Nishida; Kei Toriyabe; Ryouta Taguchi; Jiro Motoyoshiya; Yoshinori Nishii
• Keywords: 01 natural sciences; 0104 chemical sciences

Abstract A novel ring-expansion of methyl (arylhydroxymethyl)cyclopropanecarboxylates 1 using Sc(OTf)3 or BF3·OEt2 afforded 1,2-dihydronaphthalene-3-carboxylic acid ester 2 in high to excellent yields. In the reaction, highly regioselective ring opening of cyclopropane and sequential cyclization occurred.