Lewis Acid‐Catalyzed Intramolecular [3 + 2] Cross‐Cycloaddition of Donor‐ Acceptor Epoxides with Alkenes for Construction of Oxa‐[<i>n</i>.2.1] Skeletons

Chen, Lu; Tian, Jun; Zhan, Yizhou; Ren, Jing; Wang, Zhongwen

doi:10.1002/cjoc.201900114

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Cited by 4 publications

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Au(I)‐Catalyzed 6‐endo‐dig Cyclizations of Aromatic 1,5‐Enynes to 2‐(Naphthalen‐2‐yl)anilines Leading to Divergent Syntheses of Benzo[α]carbazole, Benzo[c,h]cinnoline and Dibenzo[i]phenanthridine Derivatives

Wang

et al. 2021

Chin. J. Chem.

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Comprehensive Summary A gold(I)‐catalyzed 6‐endo‐dig cyclization of aromatic 1,5‐enynes was developed to synthesize 2‐(naphthalen‐2‐yl)anilines. The functional group tolerance of this cyclization was examined systematically and a possible mechanism was proposed. The derivatization of 2‐(naphthalen‐2‐yl)aniline was carried out to facile access to benzo[α]carbazole, benzo[c,h]cinnoline and dibenzo[i]phenanthridine derivatives in a divergent way.

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Au(I)‐Catalyzed 6‐endo‐dig Cyclizations of Aromatic 1,5‐Enynes to 2‐(Naphthalen‐2‐yl)anilines Leading to Divergent Syntheses of Benzo[α]carbazole, Benzo[c,h]cinnoline and Dibenzo[i]phenanthridine Derivatives

Wang

et al. 2021

Chin. J. Chem.

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Highly Z‐Selective Synthesis of Highly Substituted 1,3‐Oxathiolane‐2‐imines via TfOH‐Catalyzed Formal [3+2] Cycloaddition of Donor‐Acceptor Oxiranes and Isothiocyanates

Zhan

Wang

et al. 2021

ChemistrySelect

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TfOH-catalyzed [3 + 2] cycloaddition of donor-acceptor oxiranes with isothiocyanates via chemoselective CÀ O bond breakage of DÀ A oxiranes was developed under metal-and additive-free conditions. This method providing a facile access to a diverse range of highly substituted 1,3-oxathiolane-2-imines in good to excellent yields and with high Z-selectivity and excellent functional group tolerance. In addition, the established protocol can be easily scaled up to gram level in excellent yield. Furthermore, transformation of cycloadduct into 1,3-oxathiolane-2-one by acid hydrolysis of the imino group is easily achieved in moderate yield.

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Seven-membered rings

Meyer

Bissember

Hyland

et al. 2021

Progress in Heterocyclic Chemistry

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Lewis Acid‐Catalyzed Intramolecular [3 + 2] Cross‐Cycloaddition of Donor‐ Acceptor Epoxides with Alkenes for Construction of Oxa‐[n.2.1] Skeletons

Cited by 4 publications

References 79 publications

Au(I)‐Catalyzed 6‐endo‐dig Cyclizations of Aromatic 1,5‐Enynes to 2‐(Naphthalen‐2‐yl)anilines Leading to Divergent Syntheses of Benzo[α]carbazole, Benzo[c,h]cinnoline and Dibenzo[i]phenanthridine Derivatives

Au(I)‐Catalyzed 6‐endo‐dig Cyclizations of Aromatic 1,5‐Enynes to 2‐(Naphthalen‐2‐yl)anilines Leading to Divergent Syntheses of Benzo[α]carbazole, Benzo[c,h]cinnoline and Dibenzo[i]phenanthridine Derivatives

Highly Z‐Selective Synthesis of Highly Substituted 1,3‐Oxathiolane‐2‐imines via TfOH‐Catalyzed Formal [3+2] Cycloaddition of Donor‐Acceptor Oxiranes and Isothiocyanates

Seven-membered rings

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