東華大學圖書館 |

Language: English

Help

回圖書館首頁

手機版館藏查詢

Back

Switch To: Labeled | MARC Mode | ISBD

Inter- and Intramolecular Transition...

Bagale, Bijaya,

Linked to FindBook

Google Book

Amazon

博客來

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

Record Type:	Electronic resources : Monograph/item
Title/Author:	Inter- and Intramolecular Transition Metal-Catalyzed Reactions of α-Alkyl-α-Diazoesters // Bijaya Bagale.
Author:	Bagale, Bijaya,
Description:	1 electronic resource (399 pages)
Notes:	Source: Dissertations Abstracts International, Volume: 86-07, Section: B.
Contained By:	Dissertations Abstracts International86-07B.
Subject:	Chemistry. -
Online resource:	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 /
LDR:03281nmm a22004573i 4500 001 2438925
005 20260727135851.5
006 m o d
007 cr|nu||||||||
008 261011s2025 miu||||||m |||||||eng d
020 $a 9798346880059
035 $a (MiAaPQD)AAI31867837
035 $a (MiAaPQD)OhioLINKkent1734628766464078
035 $a AAI31867837
040 $a MiAaPQD $b eng $c MiAaPQD $e rda
100 1 $a Bagale, Bijaya, $e author. $3 3830368
245 1 0 $a Inter- and Intramolecular Transition Metal-Catalyzed Reactions of α-Alkyl-α-Diazoesters / $c Bijaya Bagale.
264 1 $a Ann Arbor : $b ProQuest Dissertations & Theses, $c 2025
300 $a 1 electronic resource (399 pages)
336 $a text $b txt $2 rdacontent
337 $a computer $b c $2 rdamedia
338 $a online resource $b cr $2 rdacarrier
500 $a Source: Dissertations Abstracts International, Volume: 86-07, Section: B.
500 $a Advisors: Mighion, Jeffrey D. Committee members: Fenk, Christopher J.; Zheng, Yaorong; Lamichhaney, Sangeet; Dunne, Keiran.
502 $b Ph.D. $c Kent State University $d 2025.
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.
546 $a English
590 $a School code: 0101
650 4 $a Chemistry. $3 516420
650 4 $a Biochemistry. $3 518028
650 4 $a Organic chemistry. $3 523952
653 $a α-alkyl-α-diazoesters
653 $a Dirhodium catalysts
653 $a Metal-carbene
653 $a Enantioselective cyclopropanation
653 $a Intramolecular transition
653 $a Lactone synthesis
690 $a 0485
690 $a 0487
690 $a 0490
710 2 $a Kent State University. $b College of Arts and Sciences / Department of Chemistry and Biochemistry. $e degree granting institution. $3 3830369
720 1 $a Mighion, Jeffrey D. $e degree supervisor.
773 0 $t Dissertations Abstracts International $g 86-07B.
790 $a 0101
791 $a Ph.D.
792 $a 2025
856 4 0 $u https://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=31867837