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

被引：30

作者：

Okada, Megumi ^{[1
]}

Yamada, Keiichi ^{[1
]}

Fukuyama, Takahide ^{[1
]}

Ravelli, Davide ^{[2
]}

Fagnoni, Maurizio ^{[2
]}

Ryu, Ilhyong ^{[1
]}

机构：

[1] Osaka Prefecture Univ, Grad Sch Sci, Dept Chem, Sakai, Osaka 5998531, Japan

[2] Univ Pavia, Dept Chem, PhotoGreen Lab, I-27100 Pavia, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 18期

关键词：

GAMMA; DELTA-UNSATURATED CARBONYL-COMPOUNDS; ALKYL IODIDES; DECATUNGSTATE; CYCLIZATION; CONVERSION; PHOTOCHEMISTRY; ACTIVATION; CHEMISTRY; ACYLATION; ALDEHYDES;

D O I：

10.1021/acs.joc.5b01850

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：9365 / 9369

页数：5

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