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   Articles with "radical cyclization" as a keyword



Novel Radical Cyclization Cascade for the Unified Synthesis of the Cedrane and Clovane Sesquiterpene Skeletons

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recommendations! Published in 2024 at "Asian Journal of Organic Chemistry"

DOI: 10.1002/ajoc.202400242

Abstract: Radical cyclization cascade reactions of epoxycyclohexanes possessing alkene and alkyne side chains have been achieved. Sequential 5‐ or 6‐exo‐trig/5‐exo‐dig reactions triggered by epoxide ring opening with Cp2TiCl were found to provide a useful unified synthetic… read more here.

Keywords: cyclization; radical cyclization; novel radical; cedrane ... See more keywords

Cerium(IV) based oxidative free radical cyclization of active methylene compounds with some cyclic alkenes: A useful annulation method for terpene functionalization

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recommendations! Published in 2019 at "Tetrahedron"

DOI: 10.1016/j.tet.2019.03.039

Abstract: Abstract Ceric ammonium nitrate-mediated oxidative cyclizations of CH-acids with terpenes and terpene like substrates were investigated. Dimedone, acetylacetone, and methyl nitroacetate were condensed with pinene, norbornene, nopol, camphene, and carvone and the reaction stereoselectivity was… read more here.

Keywords: free radical; radical cyclization; annulation; cerium based ... See more keywords

Directed Copper-Catalyzed Tandem Radical Cyclization Reaction of Alkyl Bromides and Unactivated Olefins.

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recommendations! Published in 2022 at "Organic letters"

DOI: 10.1021/acs.orglett.2c00835

Abstract: The free radical cyclization reaction is a promising strategy for ring framework formation. Herein, we report a copper-catalyzed tandem radical cyclization strategy for preparing substituted lactam derivatives. This reaction proceeds through a radical coupling approach,… read more here.

Keywords: copper catalyzed; cyclization; radical cyclization; cyclization reaction ... See more keywords

Polar-Radical Cyclization Cascades with Magnesiated Nitriles.

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recommendations! Published in 2023 at "Organic letters"

DOI: 10.1021/acs.orglett.3c01094

Abstract: Naphthalene converts magnesiated ω-alkenylnitriles into bi- and tricyclic ketones via a polar-radical addition-cyclization cascade. One-electron oxidation of magnesiated nitriles generates nitrile-stabilized radicals that cyclize onto a pendant olefin and then rebound onto the nitrile through… read more here.

Keywords: polar radical; radical cyclization; cyclization; cascades magnesiated ... See more keywords

Synthesis of the C13-C27 Fragment of Madeirolide A Using Visible-Light-Promoted Radical Cyclization.

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recommendations! Published in 2024 at "Organic letters"

DOI: 10.1021/acs.orglett.3c04305

Abstract: The convergent synthesis of a fully elaborated C13-C27 fragment of madeirolide A has been achieved. The key features of the synthesis include the stereocontrolled construction of both the THF and THP rings via visible-light-induced iridium-catalyzed… read more here.

Keywords: visible light; c27 fragment; fragment madeirolide; radical cyclization ... See more keywords

Total Synthesis of (±)-Rhazinilam via Red-Light-Driven Zinc(II)porphyrin-Catalyzed Radical Cyclization of N-Substituted Pyrrole.

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recommendations! Published in 2025 at "Organic letters"

DOI: 10.1021/acs.orglett.5c01681

Abstract: A red-light-driven radical cyclization strategy has been developed for the concise synthesis of (±)-rhazinilam. The transformation, catalyzed by [5,15-bis(pentafluorophenyl)-10,20-diphenylporphinato]zinc(II), enables the efficient formation of a tetrahydroindolizine core from an N-acyloxyphthalimide-substituted pyrrole, providing a key intermediate… read more here.

Keywords: substituted pyrrole; radical cyclization; synthesis rhazinilam; light driven ... See more keywords

Visible-Light-Promoted Selenylative Radical Cyclization of 2-Vinyl-N-Aryl Imines to 3H-Indoles via Oxygen Photosensitization.

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recommendations! Published in 2025 at "Organic letters"

DOI: 10.1021/acs.orglett.5c02670

Abstract: A visible-light-promoted tandem selenylative radical cyclization of 2-vinyl-N-aryl imines to 3H-indoles was developed involving a series of selenyl radical addition, 5-endo-trig cyclization, and redox steps. The roles of triplet oxygen (3O2) and rhodamine-sensitized singlet oxygen… read more here.

Keywords: light promoted; visible light; cyclization vinyl; cyclization ... See more keywords
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Sequential Oxidative and Reductive Radical Cyclization Approach toward Asperparaline C and Synthesis of Its 8-Oxo Analogue.

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recommendations! Published in 2017 at "Organic letters"

DOI: 10.1021/acs.orglett.7b00187

Abstract: The most advanced approach, so far, to the asperparalines is developed. Consecutive oxidative and reductive radical cyclizations serve as the key steps to stereoselectively access the complex fully elaborated skeleton containing the cyclopentane and spiro-succinimide… read more here.

Keywords: sequential oxidative; cyclization approach; radical cyclization; reductive radical ... See more keywords
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Cobalt-Catalyzed Tandem Radical Cyclization/C-C Coupling Initiated by Directed C-H Activation.

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recommendations! Published in 2019 at "Organic letters"

DOI: 10.1021/acs.orglett.9b01846

Abstract: A cobalt-N-heterocyclic carbene catalyst promotes a tandem radical cyclization/C-C coupling reaction between tosylamide-tethered bromo-alkenes and aryl N-H imines initiated by chelation-assisted arene C-H activation, affording 3-(arylmethyl)pyrrolidine derivatives in moderate to good yields. The reaction tolerates… read more here.

Keywords: tandem radical; radical cyclization; cobalt catalyzed; activation ... See more keywords
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Aroylchlorination of 1,6-Dienes via a Photoredox Catalytic Atom-Transfer Radical Cyclization Process.

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recommendations! Published in 2019 at "Organic letters"

DOI: 10.1021/acs.orglett.9b03222

Abstract: A method using aroyl chlorides as atom-transfer radical cyclization agents in a novel visible-light photocatalytic aroylchlorination reaction is developed. The overall transformation involves the formation of two new C-C bonds and one new C-Cl bond… read more here.

Keywords: atom transfer; radical cyclization; transfer radical; aroylchlorination dienes ... See more keywords

Switchable Regioselective 6-endo or 5-exo Radical Cyclization via Photoredox Catalysis.

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recommendations! Published in 2022 at "Journal of the American Chemical Society"

DOI: 10.1021/jacs.2c00192

Abstract: Controlling the regioselectivity of radical cyclizations to favor the 6-endo mode over its kinetically preferred 5-exo counterpart is difficult without introducing substrate prefunctionalization. To address this challenge, we have developed a simple method for reagent… read more here.

Keywords: catalysis; radical cyclization; endo exo; product ... See more keywords