- Deciphering DNA-based asymmetric catalysis through intramolecular Friedel-Crafts alkylations
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We describe asymmetric intramolecular Friedel-Crafts alkylations with a DNA-based hybrid catalyst and propose a plausible binding model. This study shows promise for studying relationships between the helical chirality of DNA and enantioselectivity of the chemical reaction.
- Park, Soyoung,Ikehata, Keiichi,Watabe, Ryo,Hidaka, Yuta,Rajendran, Arivazhagan,Sugiyama, Hiroshi
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p. 10398 - 10400,3
(2020/09/09)
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- A Simple Procedure for Synthesis of Roxindole, a Dopamine D2-Receptor Agonist
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A modified convenient and high yielding synthetic route for the preparation of the dopamine agonist roxindole 1 is described. The key step in our method is the phase-transfer catalyzed reaction of γ-butyrolactone with 5-methoxyindole which results in the indolylbutyric acid derivative directly in one step.
- Csende, Ferenc
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p. 253 - 254
(2007/10/03)
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- Electrophilic Substitution in Indoles. Part 11. The Mechanism of Substitution in 5-Methoxyindoles
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Deuterium labelling experiments show that the boron trifluoride-catalysed cyclisation at 90 deg C of 4-(5-methoxyindole-3-yl)butanol (1e) to 6-methoxytetrahydrocarbazole (11a) occurs by two simultaneous pathways.The main route (83.5percent) involves initial cyclisation at the 3-position of (1e) to give an intermediate spirocyclic indolenine which then rearranges to the tetrahydrocarbazole.The minor pathway (16.5percent) involves direct attack at the 2-position.A similar duality of mechanism of substitution applies to the 6-methoxy-, 4,6-dimethoxy-, and 5,6-dimethoxy-indole analogues for which the extent of substitution at the 2-position can be correlated with the calculated change in ?-electron density at the 2- and 3-positions for a series of methoxy-substituted 3-methyl-indoles.These calculations do not, however, fit the experimental findings for the 5-methoxy-derivative which appears to be anomalous, showing an unexpectedly high percentage of direct substitution at the 2-position.A possible explanation of this result is advanced.
- Clack, Denis W.,Jackson, Anthony H.,Prasitpan, Noojaree,Shannon, Patrick V. R.
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p. 909 - 916
(2007/10/02)
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