Tetrahedron letters

Competition between ester and formyl groups for control of torquoselectivity in cyclobutene electrocyclic reactions

S Niwayama, KN Houk

Index: Niwayama, Satomi; Houk, K. N. Tetrahedron Letters, 1992 , vol. 33, # 7 p. 883 - 886

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Citation Number: 33

Abstract

Abstract Methyl 3-formylcyclobutene-3-carboxylate was synthesized in five steps from commercially available cyclobutane-1, 1-dicarboxylic acid. Thermolysis afforded methyl (2H)- pyrane-5-carboxylate, which was formed by electrocyclization of the formyl-in, ester-out product of ring opening. This confirms theoretical predictions.