A Direct Approach to the cis-1-Octalone System. 2-Carbomethoxy-2-Cyclohexenone as a Dienophile

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• It should be noted that the Diels-Alder reactions of cyclohexenones with activation by an electron-withdrawing group at the β-carbon have also been reported.6 In those cases, however, different regiochemical outcome (with respect to the enone system) was obtained.6c
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• The regiochemistry wherever applicable was verified by decarbomethoxyl ation and aromatization (cf. ref. 3c) or by correlation with known compounds. The ring junction stereochemistry of all the adducts follows from the cis-principle1 for which no violations have been observed. The remaining stereochemistry was established by spectroscopic analysis including spin decoupling experiments and/or by correlation with known compounds. Details will be discussed elsewhere.
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• It is noteworthy that this stereochemical outcome is in contrast to that observed for the Lewis acid catalyzed Diels-Alder reactions involving 2-cyclohexenone and 2-methyl-2-cyclohexenone4i and hence the two processes are complementary in stereochemical control.
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