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An unusual bicyclic hydroxamate resulted from C–O bond cleavage of acylnitroso hetero-Diels–Alder cycloadducts when treated with catalytic Brønsted acids under anhydrous conditions. Similarly, the formation of a nitrone was observed using one equivalent of triflic acid.
α-Methyl β-amino diesters were synthesized in a simple three-step procedure starting from acylnitroso-derived Diels–Alder adducts of cyclopentadiene. Treatment of the cycloadducts with copper catalyst-modified methylmagnesium bromide gave anti-1,2-cyclopentenyl hydroxamic acids. Reduction of the hydroxamate NO bond with titanium(III) chloride followed by ozonolytic cleavage of the cyclopentenyl olefin...
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