Recent Advances in Catalytic Asymmetric Syntheses of Functionalized Heterocycles <i>via</i> Halogenation/Chalcogenation of Carbon‐Carbon Unsaturated Bonds

Deng, Jun; Liu, Shengshu; Zhang, Bing-Qian; Xiao, Wen-Ying; Li, Yin-Long

doi:10.1002/adsc.202200611

Cited by 20 publications

(1 citation statement)

References 186 publications

(125 reference statements)

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“…The first intramolecular haloamination reactions of amino alkenes were carried out more than a century ago [18][19][20] and this methodology allowed to increase the molecular complexity of the starting material since a ring is created together with a halide functionality suitable for further derivatizations. In addition, when the nitrogen atom is tethered on a chiral center, two additional chiral centers can be introduced on the framework with definite configuration so that a lot of highly enantioenriched amino alkenes were easily converted into chiral polysubstituted non aromatic heterocycles generally using a source of halenium ions in a basic medium, the stereoselectivity being directed by internal asymmetric induction arising from in-tether chiral centers [21][22][23][24][25][26][27].…”

Section: Introductionmentioning

confidence: 99%

Chiral non Aromatic Nitrogen-Heterocycles by Asymmetric Intramolecular Haloamination and Haloamidation

Orena*

2024

Preprint

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This review deals with the functionalization of double bonds carried out in the presence of a chiral catalyst exploiting the intramolecular attack to haliranium ions by nucleophilic nitrogen of amides or carbamates prepared from achiral aminoalkenes, and the C-N bonds formation leads to highly enantioenriched non-aromatic heterocycles. A range of protocols are reported, emphasizing the synthesis of many natural and biologically active products of pharmacological interest prepared according to this methodology.

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Section: Introductionmentioning

confidence: 99%

Chiral non Aromatic Nitrogen-Heterocycles by Asymmetric Intramolecular Haloamination and Haloamidation

Orena*

2024

Preprint

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Differentiating the Allyl and Propargyl Groups on α‐Quaternary Carboxylic Acids via Chiral Bifunctional Sulfide‐Catalyzed Kinetic Resolution

2023

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Catalytic kinetic resolution of racemic organic compounds is a reliable method to enantioselectively prepare important chiral molecules. Substrates for the kinetic resolution, however, generally required significantly different substituents at a chiral center. Catalytic kinetic resolution of racemic molecules possessing two similar substituents at a chiral center has remained a formidable challenge. In this context, we became interested in the catalytic kinetic resolution of racemic compounds bearing both allyl and propargyl groups, which are similar but useful substituents, at a chiral center. Herein, we report a kinetic resolution of αallyl-α-propargyl carboxylic acids bearing an all-carbon quaternary stereocenter via chiral bifunctional sulfidecatalyzed bromolactonization. The synthetic utility of the resultant optically active compounds obtained via kinetic resolution was also demonstrated.

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Kinetic Resolution of α‐Allyl‐α‐Cinnamyl Carboxylic Acids Bearing an All‐Carbon Quaternary Stereocenter via Bromolactonization Catalyzed by a Chiral Bifunctional Sulfide

Okuno,

Sumida,

Shirakawa

2024

Asian J Org Chem

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Catalytic kinetic resolutions of racemic carboxylic acids are important methods for preparing chiral carboxylic acids in their optically active forms. While several effective methods for the catalytic kinetic resolution of chiral α‐tertiary carboxylic acids have been reported, the efficient kinetic resolution of α‐quaternary carboxylic acids remains a significant challenge. In this context, we aimed to develop methods for the kinetic resolution of α‐quaternary carboxylic acids. Our approach involves a BINOL‐derived chiral bifunctional sulfide‐catalyzed bromolactonization technique, which was developed by our research group. In this work, we report the kinetic resolution of α‐allyl‐α‐cinnamyl carboxylic acids bearing an α‐quaternary stereocenter via chemo‐ and stereoselective bromolactonizations. The use of a BINOL‐derived chiral bifunctional sulfide catalyst with a hydroxy group was key for the efficient kinetic resolution of racemic α‐allyl‐α‐cinnamyl carboxylic acids.

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Recent Advances in Catalytic Asymmetric Syntheses of Functionalized Heterocycles via Halogenation/Chalcogenation of Carbon‐Carbon Unsaturated Bonds

Cited by 20 publications

References 186 publications

Chiral non Aromatic Nitrogen-Heterocycles by Asymmetric Intramolecular Haloamination and Haloamidation

Chiral non Aromatic Nitrogen-Heterocycles by Asymmetric Intramolecular Haloamination and Haloamidation

Differentiating the Allyl and Propargyl Groups on α‐Quaternary Carboxylic Acids via Chiral Bifunctional Sulfide‐Catalyzed Kinetic Resolution

Kinetic Resolution of α‐Allyl‐α‐Cinnamyl Carboxylic Acids Bearing an All‐Carbon Quaternary Stereocenter via Bromolactonization Catalyzed by a Chiral Bifunctional Sulfide

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