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

The Journal of Organic Chemistry
Megumi OkadaIlhyong Ryu

Abstract

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.

References

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Jan 29, 2009·The Journal of Organic Chemistry·Derrick L J Clive, Mai P Pham
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Apr 11, 2014·The Journal of Organic Chemistry·Takuji KawamotoIlhyong Ryu
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Feb 19, 2015·Organic Letters·Keiichi YamadaIlhyong Ryu
Nov 28, 2015·ChemCatChem·Sofía FerrerAntonio M Echavarren

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Citations

Feb 7, 2017·Chemical Communications : Chem Comm·Matteo C QuattriniIlhyong Ryu
Mar 23, 2019·Chemical Society Reviews·Paramasivam SivaguruXihe Bi
Oct 8, 2019·Chemical Communications : Chem Comm·Pei FanChuan Wang
Apr 30, 2017·Chemical Science·Dylan J AbramsErik J Sorensen
Dec 2, 2017·Chemistry : a European Journal·Giorgos N PapadopoulosChristoforos G Kokotos
Jul 30, 2019·ChemSusChem·Ioanna K SideriChristoforos G Kokotos
Aug 7, 2021·Chemical Reviews·Luca CapaldoMaurizio Fagnoni

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