Tetrahedron letters

Samarium diiodide-promoted intramolecular ketone–ester coupling reaction: novel cyclization and ring expansion pathway

K Iwaya, M Nakamura, E Hasegawa

Index: Iwaya, Kazuki; Nakamura, Momoe; Hasegawa, Eietsu Tetrahedron Letters, 2002 , vol. 43, # 29 p. 5067 - 5070

Full Text: HTML

Citation Number: 12

Abstract

When ethyl 2-substituted-1-indanone-2-carboxylates were treated with samarium diiodide (SmI2), ring expansion products such as 3-substituted-1, 2-naphthoquinones were isolated. Alcohols were also obtained as the mixture of cis-and trans-isomers of hydroxy and ester substituents. A reaction mechanism involving intramolecular addition of samarium ketyl radicals to ester substituents followed by ring expansion was proposed for the formation of ...