Abstract
Intramolecular Diels-Alder (IMDA) reaction of the hydroxamate-tethered 1,3,9-decatrienes has been investigated under both thermal and microwave heating, and the stereoselectivity has been revisited. It was found that a temperature-dependent rearrangement of (2E,4E)-hexadien-1-yl N-benzylhydroxamates into the corresponding (2E,4)-1-methylpentadien-1-yl derivatives took place prior to IMDA reaction upon heating, and up to four cycloadducts were identified by analysis of the crude reaction mixtures. The IMDA reaction could be accelerated with microwave irradiation at 180 ˚C in MeCN. Stereoselectivity of the microwave-assisted IMDA reaction has been examined by using the substituents appended at C1, C5, and C10 of the hydroxamate-tethered 1,3,9-decatrienes.
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