Endo Selectivity in the (4 + 3) Cycloaddition of Oxidopyridinium Ions
- 12 October 2021
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 23 (21) , 8302-8306
Abstract
The (4 + 3) cycloaddition of 2-trialkylsilyl-4-alkylbutadienes with an N-methyloxidopyridinium ion affords cycloadducts with high regioselectivity and excellent endo selectivity.Keywords
Funding Information
- Division of Chemistry (CHE-1764437)
- Australian Research Council (DP180103047)
This publication has 29 references indexed in Scilit:
- An Improved Synthesis of the Tricyclic Core of Sarains by a 3-Oxidopyridinium Betaine CycloadditionHETEROCYCLES, 2004
- 1,3-Dipolar character of six-membered aromatic rings. Part 51. Cycloadditions of 1-(β-benzoylvinyl)-3-oxidopyridiniums and subsequent transformationsJournal of the Chemical Society, Perkin Transactions 1, 1980
- 1,3-Dipolar character of six-membered aromatic rings. Part 38. FMO treatment of peri-, site, regio, and stereo-selectivity, and relative reaction rates of cycloaddition reactionsJournal of the Chemical Society, Perkin Transactions 1, 1979
- 1,3-Dipolar character of six-membered aromatic rings. Part 34. The search for superior 1-substituents to facilitate cycloadditions of 3-oxidopyridiniumJournal of the Chemical Society, Perkin Transactions 1, 1979
- 1,3-Dipolar character of six-membered aromatic rings. Part 43. Cycloadditions leading to tricyclic adductsJournal of the Chemical Society, Perkin Transactions 1, 1979
- 1,3-Dipolar character of six-membered aromatic rings. Part 33. Transformations of cycloadducts derived from 3-oxido-1-triazinylpyridiniumsJournal of the Chemical Society, Perkin Transactions 1, 1977
- 1,3-Dipolar character of six-membered aromatic rings. Part XXI. Thermal cycloadditions of 1-(5-nitro-2-pyridyl)- and 1-(4,6-dimethylpyrimidin-2-yl)-3-oxidopyridinium with 2, 4, and 6 π-electron componentsJournal of the Chemical Society, Perkin Transactions 1, 1976
- 1,3-Dipolar character of six-membered aromatic rings. Part XXV. 5-Aryl-1-methyl-3-oxidopyridiniumsJournal of the Chemical Society, Perkin Transactions 1, 1976
- Rationalisation of the variation of reactivity towards cycloaddition with structure in 3-oxido-pyridinium and -azinium betaines and a study of 1-(4,6-dimethyl-2-pyrimidinyl)-3-oxidopyridiniumJournal of the Chemical Society, Chemical Communications, 1975
- The dimer of 1-(5-nitro-2-pyridyl)-3-oxidopyridinium and its reactionsJournal of the Chemical Society, Chemical Communications, 1974