Diels-alder cycloaddition reactions of cyclopropenone ketals
1986; Elsevier BV; Volume: 42; Issue: 11 Linguagem: Inglês
10.1016/s0040-4020(01)90567-8
ISSN1464-5416
AutoresDale L. Boger, Christine E. Brotherton,
Tópico(s)Microbial Natural Products and Biosynthesis
ResumoDiels-Alder cycloadditions of the cyclopropenone ketal 1 with representative electron-deficient, electron-rich and neutral dienes are presented. The results observed are consistent with the potential for the strained olefin of the cyclopropenone ketal to exhibit accelerated participation in both inverse electron demand (LUMOdienecontrolled) and normal(HOMOdienecontrolled) Diels-Alder reactions. Approaches to the introduction of cycloheptatrienones, tropones, based on the room temperature and pressure-promoted Diels-Alder reactions of the cyclopropenone ketal 1 are presented.
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