Reactions of Dialkyl 4-Bromo-2,2-dimethyl-3-oxohexane-l,6-dioates,-heptane-l,7-dioates with Zinc and Aromatic Aldehydes

摘要

Zinc enolates generated from dimethyl 4-bromo-2,2-dimethyl-3-oxohexane-1,6-dioate and zinc reacted with aromatic aldehydes giving methyl 2,2-dimethyl-3-oxo-3-(5-oxo-2-aryltetrahydrofuran-3-yl)propanoates.The reaction of zinc enolates obtained from dimethyl 4-bromo-2,2-dimethyl-3-oxoheptane-l,7-dioate and zinc with aromatic aldehydes depending on the synthesis conditions led to the formation either methyl 2,2-dimethyl-3-oxo-3-(6-oxo-2-aryltetrahydropyran-3-yl)propanoates or 3-(5,5-dimethyl-4,6-dioxo-2-aryltetrahydropyran-3-yl)propanoates.The compounds synthesized formed as a single diastereomer of E-configuration.