Silyl Group‐Directed 6‐<i>exo</i>‐<i>dig</i> Iodocyclization of Homopropargylic Carbamates and Amides

Okitsu, Takashi; Nakahigashi, Hikaru; Sugihara, Ryosuke; Fukuda, Ikki; Tsuji, Saki; In, Yasuko; Wada, Akimori

doi:10.1002/chem.201804794

Cited by 6 publications

(1 citation statement)

References 65 publications

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“…As a selective heterocycle synthesis in the iodocyclization of alkylamides, the Wada group developed a method for O/N atom-selective cyclizations controlled by the substituent of the alkyne moiety. Treatment of silyl-(87) and aryl-functionalized substrates (87') with IPy2PF6 at room temperature led to the formation of oxazines 88 [95] and 2,3-dihydropyrroles 88' [63], respectively. The authors explained that the controlling factor of the O/N selectivity in these iodocyclizations was due to the both β-silyl and resonance effects ( Figure 41).…”

Section: O/n Atom-selective Cyclizationsmentioning

confidence: 99%

Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy

China

Kumar

Kikushima

et al. 2020

Preprint

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In organic synthesis, due to their high electrophilicity and leaving group properties, halogens play pivotal roles in the activation and structural derivations of organic compounds. Recently, cyclizations induced by halogen groups that allow the production of diverse targets and the structural reorganization of organic molecules have attracted significant attention from synthetic chemists. Electrophilic halogen atoms activate unsaturated and saturated hydrocarbon moieties via the generation of halonium intermediates, followed by the attack of carbon-, nitrogen-, oxygen-, and sulfur-containing nucleophiles to give highly functionalized carbo- and heterocycles. Interestingly, new transformations of halogenated organic molecules that can control the formation and stereoselectivity of the products according to the difference in the size and number of halogen atoms have recently been discovered. These unique cyclizations may possibly be used as efficient synthetic strategies with future advances. In this review, innovative reactions controlled by halogen groups are discussed as a new concept in the field of organic synthesis.

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Section: O/n Atom-selective Cyclizationsmentioning

confidence: 99%

Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy

China

Kumar

Kikushima

et al. 2020

Preprint

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Switchable Regioselective 7-endo or 6-exo Iodocyclization of O-Homoallyl Benzimidates

Cao

Wang

2023

J. Org. Chem.

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We present a facile switchable regioselective 7-endo or 6-exo iodocyclization of O-homoallyl benzimidates here, which affords various iodo-substituted 1,3-oxazines and tetrahydro-1,3-oxazepines in a controllable manner. The products can further undergo substitution reactions to afford a series of rich functionalized target heterocyclic molecules. The developed protocol has the advantages of mild conditions, simple operation, and excellent functional group compatibility.

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Phosphazene Superbase-Mediated Regio- and Stereoselective Iodoaminocyclization of 2-(1-Alkynyl)benzamides for the Synthesis of Isoindolin-1-ones

Mehta

Brahmchari

2019

J. Org. Chem.

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Phosphazene superbase P 4 -t-Bu mediated iodoaminocyclization of 2-(1-alkynyl)benzamides is reported. The reaction works under ambient conditions and instantaneously results in the synthesis of isoindolin-1-ones in 65−97% yields, in a regio-and stereoselective manner. The exclusive formation of products with Z-geometry (across the exo CC bond) has been confirmed through X-ray crystallography. The methodology also provides an easy access to aristolactams, an important class of natural products. This has been successfully demonstrated by synthesizing two aristolactam derivatives (including Cepharanone B).

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Silyl Group‐Directed 6‐exo‐dig Iodocyclization of Homopropargylic Carbamates and Amides

Cited by 6 publications

References 65 publications

Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy

Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy

Switchable Regioselective 7-endo or 6-exo Iodocyclization of O-Homoallyl Benzimidates

Phosphazene Superbase-Mediated Regio- and Stereoselective Iodoaminocyclization of 2-(1-Alkynyl)benzamides for the Synthesis of Isoindolin-1-ones

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