Regio- and Stereochemically Controlled Formation of Hydroxamic Acid Containing a nti - or s yn -1,4-Cycloalkenols from Acylnitroso-Derived DielsAlder Adducts
摘要：
Treatment of acylnitroso hetero DielsAlder cycloadducts 2 with iron(III) or copper(II) in an alcohol solvent induces ring opening to afford predominantly monocyclic anti-1,4-hydroxamic acids 3. However, treatment of cycloadducts 2 with copper(II) in toluene reverses the stereoselectivity of the ring opening to afford syn-1,4-hydroxamic acids 4. These regio- and stereoselective processes separately provide anti-1,4- and syn-1,4-disubstituted cyclopentenes while regenerating a hydroxamic acid moiety, thus enhancing the chemical versatility of the DielsAlder cycloadducts.
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DOI：
10.1021/jo010094a
年份：
2001
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