Abstract
The hetero-Diels-Alder reaction of 2-methyl-1-(1-phenylalkoxy)-butadienes 5a-d with cyclic triketones proceeds smoothly at room temperature in excellent yield and high diastereoselectivity. The configuration of the cycloadducts 6a and 6b was determined by X-ray single crystal analysis. Mild acidic hydrolysis of the cycloadduct 6a using SiO2 as a promoter yielded an α,β-unsaturated aldehyde trans-9. The trans-epoxides 10a-d can be obtained from 6a-d using a freshly prepared solution of dimethyldioxirane in acetone.
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