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Inter- and Intramolecular Transition...

Bagale, Bijaya,

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Inter- and Intramolecular Transition Metal-Catalyzed Reactions of α-Alkyl-α-Diazoesters /

紀錄類型:	書目-電子資源 : Monograph/item
正題名/作者:	Inter- and Intramolecular Transition Metal-Catalyzed Reactions of α-Alkyl-α-Diazoesters // Bijaya Bagale.
作者:	Bagale, Bijaya,
面頁冊數:	1 electronic resource (399 pages)
附註:	Source: Dissertations Abstracts International, Volume: 86-07, Section: B.
Contained By:	Dissertations Abstracts International86-07B.
標題:	Chemistry. -
電子資源:	https://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=31867837
ISBN:	9798346880059

Inter- and Intramolecular Transition Metal-Catalyzed Reactions of α-Alkyl-α-Diazoesters /
Bagale, Bijaya,

Inter- and Intramolecular Transition Metal-Catalyzed Reactions of α-Alkyl-α-Diazoesters /Bijaya Bagale. - 1 electronic resource (399 pages)

Source: Dissertations Abstracts International, Volume: 86-07, Section: B.

This dissertation explores the inter- and intramolecular transition metal-catalyzed reactions of α-alkyl-α-diazoesters, highlighting their potential as versatile reagents in asymmetric synthesis. Despite the potential use in organic syntheses, α-alkyl-α-diazoesters face significant limitations due to α-hydride migration, which leads to undesirable alkene formation and restricts their utility in valuable CαH insertion reactions.In this research, a novel class of electron-deficient α-alkyl-α-diazoesters was designed and synthesized to minimize or eliminate α-hydride migration. A three-step synthetic route has been developed (up to 73% yield for three steps), enabling the successful application of these diazoesters in Rh-catalyzed enantioselective cyclopropanation reactions with high diastereo- and enantioselectivity (up to 99% yield, 97: 3 dr, 93% ee). Additionally, the dissertation discusses the development of a dirhodium(II)-catalyzed intramolecular CαH insertion method to generate lactones from α-alkyl-α-diazoesters (21 examples, up to 96% yield), as well as the exploration of dirhodium(II)-catalyzed intermolecular CαH insertions to functionalize 1,4-cyclohexadiene (up to 56% yield, 87% ee) and benzyl derivatives (72%, 82% ee).The findings aim to address existing challenges in CαH bond functionalization, ultimately contributing to more efficient and selective synthetic methodologies in organic chemistry. This research not only enhances the understanding of α-alkyl-α-diazoesters but also opens new avenues for their application in the synthesis of complex molecules, including valuable intermediates in natural product chemistry.

English

ISBN: 9798346880059Subjects--Topical Terms:

516420
Chemistry.
Subjects--Index Terms:

α-alkyl-α-diazoesters

Inter- and Intramolecular Transition Metal-Catalyzed Reactions of α-Alkyl-α-Diazoesters /
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520 $a This dissertation explores the inter- and intramolecular transition metal-catalyzed reactions of α-alkyl-α-diazoesters, highlighting their potential as versatile reagents in asymmetric synthesis. Despite the potential use in organic syntheses, α-alkyl-α-diazoesters face significant limitations due to α-hydride migration, which leads to undesirable alkene formation and restricts their utility in valuable CαH insertion reactions.In this research, a novel class of electron-deficient α-alkyl-α-diazoesters was designed and synthesized to minimize or eliminate α-hydride migration. A three-step synthetic route has been developed (up to 73% yield for three steps), enabling the successful application of these diazoesters in Rh-catalyzed enantioselective cyclopropanation reactions with high diastereo- and enantioselectivity (up to 99% yield, 97: 3 dr, 93% ee). Additionally, the dissertation discusses the development of a dirhodium(II)-catalyzed intramolecular CαH insertion method to generate lactones from α-alkyl-α-diazoesters (21 examples, up to 96% yield), as well as the exploration of dirhodium(II)-catalyzed intermolecular CαH insertions to functionalize 1,4-cyclohexadiene (up to 56% yield, 87% ee) and benzyl derivatives (72%, 82% ee).The findings aim to address existing challenges in CαH bond functionalization, ultimately contributing to more efficient and selective synthetic methodologies in organic chemistry. This research not only enhances the understanding of α-alkyl-α-diazoesters but also opens new avenues for their application in the synthesis of complex molecules, including valuable intermediates in natural product chemistry.
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653 $a Lactone synthesis
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