Formation of β-lactones in the iodolactonization reaction

Barnett, William E.; Sohn, Won H.

doi:10.1016/s0040-4039(01)85266-7

Cited by 28 publications

(4 citation statements)

References 3 publications

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“…Among them, the controllable endo / exo switchable iodocyclization, which enables the selective construct of two types of valuable iodo-substituted cyclic compounds, is a more interesting and challenging research field; however, it has not been well explored . An early example of the endo / exo switchable iodolactonization reactions of olefinic acids was realized by Tamelen and Barnett, respectively, in which the 5- endo / 4-exo selectivity was found to be strongly influenced by the reaction conditions (Scheme a) . In 2014, the Wirth group reported an effective organocatalytic approach for the selective 6- endo / 5-exo -cyclization of olefinic N -tosylamines.…”

Section: Introductionmentioning

confidence: 99%

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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Section: Introductionmentioning

confidence: 99%

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

Cao

Wang

2023

J. Org. Chem.

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“…In 1953, Tamelen and Shamma reported the iodolactonization of olefinic acid 1 to obtain γ-lactone 2 ( Figure 2 ) [ 3 ]. In 1972, Barnett and Sohn then reported the selective iodolactonization of the same olefinic acid 1 to alternatively synthesize β-lactone 2′ [ 21 ]. From these studies, the endo / exo selectivity of iodolactonizations was found to be strongly influenced by the reaction conditions and combination of the reagents.…”

Section: Introductionmentioning

confidence: 99%

Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy

et al. 2020

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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 by generating halonium intermediates, followed by the attack of carbon-containing, nitrogen-containing, oxygen-containing, and sulfur-containing nucleophiles to give highly functionalized carbocycles and heterocycles. 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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“…In 1953, Tamelen and Shamma reported the iodolactonization of olefinic acid 1 to obtain γ-lactone 2 ( Figure 2) [21]. In 1972, Barnett and Sohn then reported the selective iodolactonization of the same olefinic acid 1 to alternatively synthesize β-lactone 2' [22]. From these studies, the endo/exo selectivity of iodolactonizations was found to be strongly influenced by the reaction conditions and combination of the reagents.…”

Section: Introductionmentioning

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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Formation of β-lactones in the iodolactonization reaction

Cited by 28 publications

References 3 publications

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

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

Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy

Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy

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