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Beilstein J Org Chem. 2012;8:650-7. Epub 2012 Apr 26.

Alkoxide-induced ring opening of bicyclic 2-vinylcyclobutanones: A convenient synthesis of 2-vinyl-substituted 3-cycloalkene-1-carboxylic acid esters.

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1
Department of Chemistry, Fudan University, 220 Handan Road, 200433 Shanghai, P. R. China.

Abstract

The fused 2-vinyl or 2-phenyl substituted cyclobutanones 4 undergo stereoselective ring openings by the action of alkoxide ions (t-BuO(-) or MeO(-)) to produce novel vicinally disubstituted cycloalkene derivatives 5 and 6 in moderate to high yields. The ring cleavage usually occurs with complete regioselectivity. The accessibility of γ,δ-unsaturated ester or acid derivatives makes this transformation a good supplementary method for the well-established Johnson-Claisen rearrangement.

KEYWORDS:

alkoxide; cyclobutanones; esters; fused ring systems; ring opening

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