Photocatalytic One-Pot Synthesis of Homoallyl Ketones via a Norrish Type I Reaction of Cyclopentanones

A photocatalytic synthesis of homoallyl ketones was achieved via a one-pot procedure starting from a Norrish Type I reaction of cyclopentanones, followed by a decatungstate-catalyzed hydroacylation of electron-deficient olefins by the resulting 4-pentenals. The site-selective formyl H-abstraction in...

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Veröffentlicht in:Journal of organic chemistry 2015-09, Vol.80 (18), p.9365-9369
Hauptverfasser: Okada, Megumi, Yamada, Keiichi, Fukuyama, Takahide, Ravelli, Davide, Fagnoni, Maurizio, Ryu, Ilhyong
Format: Artikel
Sprache:eng
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Zusammenfassung:A photocatalytic synthesis of homoallyl ketones was achieved via a one-pot procedure starting from a Norrish Type I reaction of cyclopentanones, followed by a decatungstate-catalyzed hydroacylation of electron-deficient olefins by the resulting 4-pentenals. The site-selective formyl H-abstraction in the second step can be explained by radical polar effects in the transition state.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b01850