Journal
ORGANIC LETTERS
Volume 9, Issue 20, Pages 3893-3896Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol701496b
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UVA irradiation (ca. 350 nm) of a mixture of cyclic enones and nitrogen heterocycles leads to efficient formation of the 1,4-adducts in a variety of solvents, at room temperature. These reactions likely proceed through strained E-cycloalkenone intermediates, as suggested by low-temperature generation/trapping experiments monitored by H-1 NMR. These results demonstrate that E-cycloalkenones are good electrophiles despite their known tendency to favor a conformation in which the carbonyl is not fully conjugated with the double bond.
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