Regioselective synthesis of α, α-dialkylcyclopentanones from 1-hydroxycyclobutanecarboxylic acid or from O-protected cyclobutanone cyanohydrin

K Estieu, J Ollivier, J Salaün

Index: Estieu, Karine; Ollivier, Jean; Salauen, Jacques Tetrahedron, 1998 , vol. 54, # 28 p. 8075 - 8090

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Citation Number: 10

Abstract

1-(1-Hydroxyalkyl) cylobutanols 4a-f, readily available either from 1-hydroxycyclobutane carboxylic acid or from O-protected cyclobutanone cyanohydrin, appeared the most suitable precursors for a regioselective synthesis of cyclopentanones α, α-disubstituted with various similar or different alkyl, alkenyl, aryl or cycloalkyl groups. The key steps consist of acid or Grignard reagent induced C4→ C5 ring expansions.