A chiral scandium-complex-catalyzed asymmetric inverse-electron-demand oxa-Diels–Alder reaction of o-quinone methides with fulvenes

2018 ◽  
Vol 54 (1) ◽  
pp. 74-77 ◽  
Author(s):  
Jianlin Zhang ◽  
Lili Lin ◽  
Changqiang He ◽  
Qian Xiong ◽  
Xiaohua Liu ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Optically Active ◽  
Diels Alder ◽  
Quinone Methides ◽  
Inverse Electron Demand ◽  
Highly Efficient ◽  
Diels Alder Reaction ◽  
High Yields ◽  
Electron Demand

A highly efficient asymmetric [4+2] cycloaddition of o-quinone methides with fulvenes has been realized using a chiral N,N′-dioxide/Sc(iii) complex as the catalyst. The corresponding optically active chromane derivatives were obtained in high yields with excellent dr and ee values.

scholarly journals Combination of inverse electron-demand Diels–Alder reaction with highly efficient oxime ligation expands the toolbox of site-selective peptide conjugations

2015 ◽  
Vol 51 (55) ◽  
pp. 11130-11133 ◽  
Author(s):  
S. Hörner ◽  
C. Uth ◽  
O. Avrutina ◽  
H. Frauendorf ◽  
M. Wiessler ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Inverse Electron Demand ◽  
Highly Efficient ◽  
Diels Alder Reaction ◽  
Site Selective ◽  
Electron Demand

A modular bioconjugation strategy based on stepwise oxime ligation and inverse electron-demand Diels–Alder reaction.

scholarly journals Synthesis of dibenzosuberenone-based novel polycyclic π-conjugated dihydropyridazines, pyridazines and pyrroles

2021 ◽  
Vol 17 ◽  
pp. 719-729
Author(s):  
Ramazan Koçak ◽  
Arif Daştan
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Cycloaddition Reactions ◽  
Inverse Electron Demand ◽  
Diels Alder Reaction ◽  
Reductive Treatment ◽  
High Yields ◽  
Derivatives Of ◽  
Electron Demand

The synthesis of novel polycyclic π-conjugated dihydropyridazines, pyridazines, and pyrroles was studied. Dihydropyridazine dyes were synthesized by inverse electron-demand Diels–Alder cycloaddition reactions between a dibenzosuberenone and tetrazines that bear various substituents. The pyridazines were synthesized in high yields by oxidation of dihydropyridazine-appended dibenzosuberenones with PIFA or NO. p-Quinone derivatives of pyridazines were also obtained by H-shift isomerization following the inverse electron-demand Diels–Alder reaction of tetrazines with p-quinone dibenzosuberenone. Then these pyridazines were converted to the corresponding pyrroles by reductive treatment with zinc. It was observed that all the dihydropyridazines obtained gave absorbance and emission at long wavelengths.

Highly efficient method for 125I-radiolabeling of biomolecules using inverse-electron-demand Diels–Alder reaction

2016 ◽  
Vol 24 (11) ◽  
pp. 2589-2594 ◽  
Author(s):  
Mi Hee Choi ◽  
Ha Eun Shim ◽  
Seong-Jae Yun ◽  
Hye Rim Kim ◽  
Sajid Mushtaq ◽  
...  
Keyword(s):  
Efficient Method ◽  
Alder Reaction ◽  
Diels Alder ◽  
Inverse Electron Demand ◽  
Highly Efficient ◽  
Diels Alder Reaction ◽  
Electron Demand

An Inverse Electron Demand Azo-Diels–Alder Reaction ofo-Quinone Methides and Imino Ethers: Synthesis of Benzocondensed 1,3-Oxazines

2018 ◽  
Vol 83 (8) ◽  
pp. 4775-4785 ◽  
Author(s):  
Dmitry V. Osipov ◽  
Vitaly A. Osyanin ◽  
Guzel’ D. Khaysanova ◽  
Elvira R. Masterova ◽  
Pavel E. Krasnikov ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Quinone Methides ◽  
Inverse Electron Demand ◽  
Diels Alder Reaction ◽  
Electron Demand

scholarly journals Convenient Synthesis of Functionalized Unsymmetrical Vinyl Disulfides and Their Inverse Electron-Demand Hetero-Diels-Alder Reaction

Materials ◽  
2021 ◽  
Vol 14 (6) ◽  
pp. 1342
Author(s):  
Bartosz Jędrzejewski ◽  
Mateusz Musiejuk ◽  
Justyna Doroszuk ◽  
Dariusz Witt
Keyword(s):  
Functional Groups ◽  
Alder Reaction ◽  
Diels Alder ◽  
Inverse Electron Demand ◽  
Mild Conditions ◽  
Diels Alder Reaction ◽  
Convenient Synthesis ◽  
High Yields ◽  
Electron Demand

The simple, convenient, and efficient methods for the preparation of unsymmetrical vinyl disulfides with additional functional groups under mild conditions with moderate to high yields were designed. The developed methods include the reaction of S-vinyl phosphorodithioate with thiotosylates or S-vinyl thiotosylate with thiols. The designed methods allow for the synthesis of unsymmetrical vinyl disulfides with additional functionalities such as hydroxy, carboxy, protected amino, or ester groups. Vinyl disulfides reacted with the generated transient o-iminothioquinones in an inverse electron-demand [4+2] cycloaddition to produce benzo[b][1,4]thiazine derivatives.

scholarly journals Correction: Combination of inverse electron-demand Diels–Alder reaction with highly efficient oxime ligation expands the toolbox of site-selective peptide conjugations

2015 ◽  
Vol 51 (58) ◽  
pp. 11727-11727 ◽  
Author(s):  
S. Hörner ◽  
C. Uth ◽  
O. Avrutina ◽  
H. Frauendorf ◽  
M. Wiessler ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Inverse Electron Demand ◽  
Highly Efficient ◽  
Diels Alder Reaction ◽  
Site Selective ◽  
Electron Demand

Correction for ‘Combination of inverse electron-demand Diels–Alder reaction with highly efficient oxime ligation expands the toolbox of site-selective peptide conjugations’ by S. Hörner, et al., Chem. Commun., 2015, DOI: 10.1039/c5cc03434e.

The stereoselective formation of highly substituted CF3-dihydropyrans as versatile building blocks

2015 ◽  
Vol 51 (71) ◽  
pp. 13666-13669 ◽  
Author(s):  
Bjarke S. Donslund ◽  
Alicia Monleón ◽  
Jesper Larsen ◽  
Lise Ibsen ◽  
Karl Anker Jørgensen
Keyword(s):  
Building Blocks ◽  
Alder Reaction ◽  
Optically Active ◽  
Diels Alder ◽  
Inverse Electron Demand ◽  
Diels Alder Reaction ◽  
Formal Inverse ◽  
Electron Demand

The dienamine-mediated formal inverse electron demand hetero Diels–Alder reaction providing optically active 5-bromo-6-(trifluoromethyl)-3,4-dihydro-2H-pyrans is disclosed along with interesting transformations, affording a large variety of fully substituted dihydropyrans.

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