Citation: Zhang Jian, Wu Jin-Long. Tandem intramolecular Diels-Alder/retro-Diels-Alder cycloaddition of 2H-chromen-2-one as dienes with the expulsion of CO₂[J]. Chinese Chemical Letters, ;2016, 27(9): 1537-1540. doi: 10.1016/j.cclet.2016.03.034 shu

Tandem intramolecular Diels-Alder/retro-Diels-Alder cycloaddition of 2H-chromen-2-one as dienes with the expulsion of CO₂

Zhang Jian ,
Wu Jin-Long ^,

Laboratary of Asymmetry Catalysis and synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, China

Corresponding author: Wu Jin-Long, wyz@zju.edu.cn
Received Date: 15 February 2016
Revised Date: 2 March 2016
Accepted Date: 30 March 2016
Available Online: 15 September 2016

Figures(6)

To study the intramolecular Diels-Alder cycloadditon of 2H-chromen-2-one as a diene, a series of chiral N-allyl-N-benzylamides that contain a 2H-chromen-2-one moiety were designed for the synthesis of benzo[f]isoindol-1-ones via an intramolecular Diels-Alder and a subsequent retro-Diels-Alder cycloaddition with the expulsion of CO₂. Both the yield (80%-89%) and absolute stereocontrol of the tandem reaction were high when an electron-withdrawing group was attached to the dienophile. The double bond in the styrene substructure remained in the products could be further derivatized by dihydroxylation.
- 2H-Chromen-2-one,
- Intramolecular Diels-Alder,
- Retro-Diels-Alder,
- Benzo[f]isoindol-1-one,
- Dihydroxylation
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沈阳化工大学材料科学与工程学院沈阳 110142

Tandem intramolecular Diels-Alder/retro-Diels-Alder cycloaddition of 2H-chromen-2-one as dienes with the expulsion of CO2

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通讯作者: 陈斌, bchen63@163.com

Tandem intramolecular Diels-Alder/retro-Diels-Alder cycloaddition of 2H-chromen-2-one as dienes with the expulsion of CO₂