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 DOI
Feng Zhan, Zhe Wang, Guanzheng Wu

et al.

ChemistrySelect, Journal Year: 2021, Volume and Issue: 6(13), P. 3151 - 3154

Published: April 1, 2021

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

Language: Английский

Seven-membered rings DOI
Adam G. Meyer, Alex C. Bissember, Christopher J. T. Hyland

et al.

Progress in heterocyclic chemistry, Journal Year: 2021, Volume and Issue: unknown, P. 565 - 614

Published: Jan. 1, 2021

Language: Английский

Citations

9
Asymmetric Cycloadditions of Acyclic Carbonyl Ylides with Aldehydes Catalyzed by a Chiral Binaphthyldiimine-Ni(II) Complex: Enantioselective Synthesis of 1,3-Dioxolanes and Mechanistic Studies by DFT Calculations DOI
Yasunori Toda,

Kayo Sato,

Kensuke Sato

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(26), P. 4739 - 4744

Published: June 20, 2022

Chiral binaphthyldiimine-Ni(II)-catalyzed asymmetric 1,3-dipolar cycloaddition reactions between acyclic carbonyl ylides generated from donor-acceptor oxiranes and aldehydes are reported. Both aromatic aliphatic could be used as dipolarophiles, providing cis-1,3-dioxolanes with high diastereo- enantioselectivities. On the basis of mechanistic studies, a monomeric chiral Ni(II) complex was hypothesized to act active species for cycloaddition. The levels induction satisfactorily explained by concerted-asynchronous endo Si-face approach aldehyde.

Language: Английский

Citations

6
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 DOI

Jiayue Fu,

Bingbing Li, Xiugui Wang

et al.

Chinese Journal of Chemistry, Journal Year: 2021, Volume and Issue: 40(1), P. 46 - 52

Published: Oct. 13, 2021

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 this examined systematically and a possible mechanism proposed. derivatization 2‐(naphthalen‐2‐yl)aniline carried out facile access benzo[ α ]carbazole, c , h ]cinnoline dibenzo[ i ]phenanthridine derivatives in divergent way.

Language: Английский

Citations

3
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 DOI
Feng Zhan, Zhe Wang, Guanzheng Wu

et al.

ChemistrySelect, Journal Year: 2021, Volume and Issue: 6(13), P. 3151 - 3154

Published: April 1, 2021

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

Language: Английский

Citations

1