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Mechanism and Regioselectivity of an Unsymmetrical Hexadehydro-Diels–Alder (HDDA) Reaction
- Chen, Maggie, He, Cyndi Qixin, Houk, K. N.
- Journal of organic chemistry 2019 v.84 no.4 pp. 1959-1963
- amines, chemical reactions, chemical structure, density functional theory, organic chemistry, phenols, regioselectivity
- Hoye reported intramolecular hexadehydro-Diels–Alder (HDDA) reactions to generate arynes that functionalize natural product phenols and amines. In their studies, Hoye found that unsymmetrical tetraynes selectively form a single aryne. We report density functional theory (DFT) calculations that reveal the factors controlling the regioselectivity.