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Nickel-Catalyzed Site- and Stereoselective Syntheses of Complex Molecular Fragments From 1,3-Dienes Through Use of Novel P,N Ligands
Nickel-Catalyzed Site- and Stereoselective Syntheses of Complex Molecular Fragments From 1,3-Dienes Through Use of Novel P,N Ligands
상세정보
- 자료유형
- 학위논문 서양
- 최종처리일시
- 20260202104803
- ISBN
- 9798291554319
- DDC
- 547
- 서명/저자
- Nickel-Catalyzed Site- and Stereoselective Syntheses of Complex Molecular Fragments From 1,3-Dienes Through Use of Novel P,N Ligands
- 발행사항
- [Sl] : The University of North Carolina at Chapel Hill, 2025
- 발행사항
- Ann Arbor : ProQuest Dissertations & Theses, 2025
- 형태사항
- 123 p
- 주기사항
- Source: Dissertations Abstracts International, Volume: 87-02, Section: B.
- 주기사항
- Advisor: Johnson, Jeffrey S.
- 학위논문주기
- Thesis (Ph.D.)--The University of North Carolina at Chapel Hill, 2025.
- 초록/해제
- 요약Alkenes are abundant feedstock chemicals which can be utilized as platforms for the construction of complex molecules bearing a variety of functional groups and stereogenic centers. Methods which focus on facilitating this rapid development of complexity while exerting site- and stereocontrol are of great importance. Olefin dicarbofunctionalization is a general reaction class which allows for the formation of two new C-C σ-bonds from an olefin π-bond allowing for a step and atom economical means of accessing functionalized molecules. Homoallylation reactions have also received attention as a means of synthesizing understudied bishomoallyl alcohols and amines from simple dienes and either aldehydes or imine substrates.Chapter 1 describes early work conducted on the dicarbofunctionalization of 1,3-alkyl dienes with aldehydes. While 1,3-alkyl dienes pose numerous challenges for selective couplings due to their smaller size, we were able to observe an improvement in site-selectivity when employing a novel pyridylphosphine ligand.Chapter 2 demonstrates the effective use of pyridylphosphine ligands in the site- and stereoselective dicarbofunctionalization of 1,3-dienes with imines and boronic ester coupling partners. We also determined that the site-selectivity of the reaction can be guided by additional substitution of the diene to form all-carbon quaternary centers selectively.Chapter 3 covers our current progress on the homoallylation of aldehydes with 1,3-dienes to form bishomoallylic alcohols. Use of our P,N ligand system allows for use non-polarized dienes for the selective synthesis of all-carbon quaternary center containing alcohol products.
- 일반주제명
- Organic chemistry
- 일반주제명
- Chemistry
- 일반주제명
- Analytical chemistry
- 키워드
- Alkenes
- 키워드
- Homoallylation
- 기타저자
- The University of North Carolina at Chapel Hill Chemistry
- 기본자료저록
- Dissertations Abstracts International. 87-02B.
- 전자적 위치 및 접속
- 로그인 후 원문을 볼 수 있습니다.
MARC
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■00520260202104803
■006m o d
■007cr#unu||||||||
■020 ▼a9798291554319
■035 ▼a(MiAaPQ)AAI32164880
■040 ▼aMiAaPQ▼cMiAaPQ
■0820 ▼a547
■1001 ▼aMickles, Devin T.
■24510▼aNickel-Catalyzed Site- and Stereoselective Syntheses of Complex Molecular Fragments From 1,3-Dienes Through Use of Novel P,N Ligands
■260 ▼a[Sl]▼bThe University of North Carolina at Chapel Hill▼c2025
■260 1▼aAnn Arbor▼bProQuest Dissertations & Theses▼c2025
■300 ▼a123 p
■500 ▼aSource: Dissertations Abstracts International, Volume: 87-02, Section: B.
■500 ▼aAdvisor: Johnson, Jeffrey S.
■5021 ▼aThesis (Ph.D.)--The University of North Carolina at Chapel Hill, 2025.
■520 ▼aAlkenes are abundant feedstock chemicals which can be utilized as platforms for the construction of complex molecules bearing a variety of functional groups and stereogenic centers. Methods which focus on facilitating this rapid development of complexity while exerting site- and stereocontrol are of great importance. Olefin dicarbofunctionalization is a general reaction class which allows for the formation of two new C-C σ-bonds from an olefin π-bond allowing for a step and atom economical means of accessing functionalized molecules. Homoallylation reactions have also received attention as a means of synthesizing understudied bishomoallyl alcohols and amines from simple dienes and either aldehydes or imine substrates.Chapter 1 describes early work conducted on the dicarbofunctionalization of 1,3-alkyl dienes with aldehydes. While 1,3-alkyl dienes pose numerous challenges for selective couplings due to their smaller size, we were able to observe an improvement in site-selectivity when employing a novel pyridylphosphine ligand.Chapter 2 demonstrates the effective use of pyridylphosphine ligands in the site- and stereoselective dicarbofunctionalization of 1,3-dienes with imines and boronic ester coupling partners. We also determined that the site-selectivity of the reaction can be guided by additional substitution of the diene to form all-carbon quaternary centers selectively.Chapter 3 covers our current progress on the homoallylation of aldehydes with 1,3-dienes to form bishomoallylic alcohols. Use of our P,N ligand system allows for use non-polarized dienes for the selective synthesis of all-carbon quaternary center containing alcohol products.
■590 ▼aSchool code: 0153.
■650 4▼aOrganic chemistry
■650 4▼aChemistry
■650 4▼aAnalytical chemistry
■653 ▼aDicarbofunctionalization
■653 ▼aAlkenes
■653 ▼aPyridylphosphine ligands
■653 ▼aHomoallylation
■653 ▼aMolecular fragments
■690 ▼a0490
■690 ▼a0486
■690 ▼a0485
■71020▼aThe University of North Carolina at Chapel Hill▼bChemistry.
■7730 ▼tDissertations Abstracts International▼g87-02B.
■790 ▼a0153
■791 ▼aPh.D.
■792 ▼a2025
■793 ▼aEnglish
■85640▼uhttp://www.riss.kr/pdu/ddodLink.do?id=T17358867▼nKERIS▼z이 자료의 원문은 한국교육학술정보원에서 제공합니다.
