Enantioselective Organocatalytic Diels-Alder Trapping of Photochemically Generated Hydroxy-o-Quinodimethanes

Angewandte Chemie
Luca Dell'AmicoPaolo Melchiorre

Abstract

The photoenolization/Diels-Alder strategy offers straightforward access to synthetically valuable benzannulated carbocyclic products. This historical light-triggered process has never before succumbed to efforts to develop an enantioselective catalytic approach. Herein, we demonstrate how asymmetric organocatalysis provides simple yet effective catalytic tools to intercept photochemically generated hydroxy-o-quinodimethanes with high stereoselectivity. We used a chiral organic catalyst, derived from natural cinchona alkaloids, to activate maleimides toward highly stereoselective Diels-Alder reactions. An unconventional mechanism of stereocontrol is operative, wherein the organocatalyst is actively involved in both the photochemical pathway, by leveraging the formation of the reactive photoenol, and the stereoselectivity-defining event.

References

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Citations

Aug 22, 2016·The Journal of Chemical Physics·Sanjiv K JhaGopinath Subramanian
Feb 12, 2017·Angewandte Chemie·Luca Dell'AmicoPaolo Melchiorre
Apr 4, 2018·Chemical Communications : Chem Comm·Javier MateosLuca Dell'Amico
Jun 12, 2018·Organic & Biomolecular Chemistry·Ioanna K SideriChristoforos G Kokotos
Aug 14, 2018·Photochemistry and Photobiology·Anushree DasAnna D Gudmundsdottir
Jan 19, 2019·Angewandte Chemie·Changsheng WuGilles P van Wezel
Feb 12, 2019·Angewandte Chemie·Caroline ApelMathias Christmann
Dec 10, 2019·Angewandte Chemie·Andreas MavroskoufisMatthew N Hopkinson
Jun 2, 2020·Chemical & Pharmaceutical Bulletin·Hiromichi Egami
Jun 3, 2016·Angewandte Chemie·Claudio E GrünenfelderHelma Wennemers
Nov 1, 2016·Chemistry : a European Journal·Moluguri RaghuS S V Ramasastry
Nov 21, 2017·Chemical Society Reviews·You-Quan ZouThorsten Bach
Feb 23, 2020·The Journal of Organic Chemistry·Suva PariaXavier Companyó
Jun 26, 2020·Organic Letters·Yanbin ZhangHao Guo
Apr 23, 2021·Journal of the American Chemical Society·Baochao YangShuanhu Gao
May 25, 2021·Journal of the American Chemical Society·Yidong LiuKarl Anker Jørgensen
May 20, 2021·Angewandte Chemie·Mengmeng XuShuanhu Gao
Jun 26, 2021·Chemical Science·Xiao-Long LuShuanhu Gao
Aug 12, 2017·Organic Letters·Takafumi IdeYoshitaka Hamashima
Jul 13, 2017·Chemical Reviews·Yan QinSanzhong Luo
Sep 23, 2021·Organic Letters·Min HouShuanhu Gao

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