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 17 publications

(1 citation statement)

References 186 publications

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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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Enantioselective Synthesis of Bromodifluoromethyl‐containing Oxazolines by Concerted Lewis/Brønsted Base Catalysis with Chiral Bisphosphine Oxide

Hirokawa

Nakahara

Uchida

et al. 2023

Chemistry An Asian Journal

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We describe regio‐ and enantioselective bromocyclization of difluoroalkenes catalyzed by chiral bisphosphine oxides. Owing to the simultaneous activation of both the brominating reagent and amide substrate, the desired cyclization reaction proceeds smoothly even at low temperature to provide bromodifluoromethyl‐containing oxazolines with a chiral quaternary center in a highly enantioselective fashion (up to 99% ee). This protocol features the use of commercially available brominating reagents and readily accessible chiral catalysts. The regioselectivity and enantioselectivity are influenced by the catalyst structure, the brominating reagent, and the reaction temperature. Under the optimal conditions, 5‐exo cyclization proceeds preferentially compared with 6‐endo cyclization, depending on the electronic properties of the alkene substrates. A gram‐scale synthesis of chiral oxazoline was achieved with as little as 1 mol % of the catalyst.

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

Cited by 17 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

Enantioselective Synthesis of Bromodifluoromethyl‐containing Oxazolines by Concerted Lewis/Brønsted Base Catalysis with Chiral Bisphosphine Oxide

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