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Polar-Radical Cyclization Cascades with Magnesiated Nitriles

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卷 25, 期 19, 页码 3512-3516

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c01094

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Naphthalene converts magnesiated omega-alkenylnitriles into bi- and tricyclic ketones via a polar-radical addition-cyclization cascade. The one-electron oxidation of magnesiated nitriles generates nitrile-stabilized radicals, which then cyclize onto a pendant olefin and rebound onto the nitrile through a reduction-cyclization sequence, followed by hydrolysis to obtain a diverse array of bicyclo[3.2.0]heptan-6-ones. Combining the polar-radical cascade with a 1,2:1,4-carbonyl-conjugate addition results in the synthesis of complex cyclobutanones containing four new carbon-carbon bonds and four chiral centers.
Naphthalene converts magnesiated omega-alkenylnitriles into bi-and tricyclic ketones via a polar-radical addition-cyclization cascade. One-electron oxidation of magnesiated nitriles generates nitrile-stabilized radicals that cyclize onto a pendant olefin and then rebound onto the nitrile through a reduction-cyclization sequence; subsequent hydrolysis affords a diverse array of bicyclo[3.2.0]heptan-6-ones. Combining the polar-radical cascade with a 1,2:1,4-carbonyl-conjugate addition generates complex cyclobutanones containing four new carbon-carbon bonds and four chiral centers in one synthetic operation.

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