Asymmetric N-H/N-alkyl olefin azirdinations and ring-opening transformations
不对称 N-H/N-烷基烯烃叠氮化和开环转化
基本信息
- 批准号:9252464
- 负责人:
- 金额:$ 32.07万
- 依托单位:
- 依托单位国家:美国
- 项目类别:
- 财政年份:2015
- 资助国家:美国
- 起止时间:2015-06-01 至 2019-03-31
- 项目状态:已结题
- 来源:
- 关键词:AlkenesAminationAminesAmino AlcoholsAntibioticsAziridinesCatalysisChemicalsChemistryCommunitiesComplexCopperDevelopmentElectronsEpoxy CompoundsEvaluationExcisionExhibitsFamilyGoalsIminesLaboratoriesLigandsMethodsNatural ProductsNitrogenOxidantsPerformancePharmaceutical ChemistryPharmaceutical PreparationsPrizeProductionPropertyReactionRhodiumRouteSynthesis ChemistryTransition Elementsalkyl groupanalogbioactive natural productscarbenecarboxylatecatalystcomputer studiescostdesignimmunoregulationnitrenenoveloperationpublic health relevancesalentertiary amine
项目摘要
DESCRIPTION (provided by applicant): Aziridines, the three-membered and equally highly-strained nitrogen analogues of epoxides, are important synthetic intermediates en route to structurally complex molecules due to their versatility in myriad regio- and stereoselective transformations. The aziridine structural motif, predominantly N-H and to a lesser extent N-alkyl, also appears in natural products which exhibit potent antibiotic, immunomodulatory and anticancer properties. Current direct olefin aziridination methods rely either on the transfer of substituted nitrenes to the C=C bond of olefins or the transfer of substituted carbenes to the C=N bond of imines. Normally, the result is an aziridine bearing a strongly electron-withdrawing N-protecting group whose removal can result in destruction of the aziridine. In addition, the high reactivity of these N-protected nitrenes can give rise to non-productive allylic C-H amination as well as the loss of stereospecificity. This proposal has two main goals: (a) the development of direct, stereospecific and practical syntheses of unprotected (i.e., N-H, N-alkyl) aziridines and (b) bis-functionalization of olefins leading to vicinally functionalized amines using homogeneous transition metal catalysis. These objectives will be developed in three specific aims: (1) Development and optimization of the direct, catalytic enantioselective N-H/N-alkyl aziridination of olefins; (2) Development of transition-metal-catalyzed direct hydro-/carbo-/heteroatom-amino olefin difunctionalizations, affording unprotected amino-alcohols, azido-amines as well as primary, secondary and tertiary amines; (3) Design and synthesis of a family of novel N-H/N-alkyl transfer agents (i.e., aminating agents) that will provide an unprecedented range of chemo- and stereo-selectivities in both direct olefin N-H/N-alkyl aziridinations and hydro-/carbo-/heteroatom-amino olefin difunctionalizations.
描述(由申请人提供):氮杂环丙烷是环氧化物的三元氮类似物,也是高度应变的氮类似物,由于其在无数区域和立体选择性转化中的多功能性,是合成结构复杂分子的重要中间体。氮杂环丙烷的结构基序,主要是N-H,少量N-烷基,也存在于天然产物中,表现出强大的抗菌、免疫调节和抗癌特性。目前的直接烯烃氮杂化方法要么依赖于取代的硝烯转移到烯烃的C=C键,要么依赖于取代卡宾转移到亚胺的C=N键。正常情况下,结果是氮杂环丙烷带有强吸电子的N-保护基团,其移除会导致氮杂环丙烷的破坏。此外,这些N-保护的硝烯的高反应性可能导致非生产性的烯丙基C-H胺化以及立体专一性的丧失。这项建议有两个主要目标:(A)开发无保护(即N-H,N-烷基)氮杂环丙烷的直接、立体专一性和实用性合成;(B)利用均相过渡金属催化使烯烃双官能化得到邻位官能化的胺。开发这些目标的具体目标有三个:(1)开发和优化直接催化的N-H/N-烷基氮烷基叠氮化反应;(2)开发过渡金属催化的直接氢化/碳/杂原子-氨基烯烃官能化反应,得到无保护的氨基醇、叠氮胺以及伯胺、仲胺和叔胺;(3)设计和合成了一系列新型的N-H/N-烷基转移剂(即胺化试剂),它们将在N-H/N-烷基氮化和氢/碳/杂原子-氨基双官能化反应中提供前所未有的化学和立体选择性。
项目成果
期刊论文数量(0)
专著数量(0)
科研奖励数量(0)
会议论文数量(0)
专利数量(0)
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Laszlo Kurti其他文献
Laszlo Kurti的其他文献
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{{ truncateString('Laszlo Kurti', 18)}}的其他基金
New catalytic methods for the rapid synthesis of N-unprotected chiral aziridines and amines
快速合成N-未保护的手性氮丙啶和胺的新催化方法
- 批准号:
10596519 - 财政年份:2020
- 资助金额:
$ 32.07万 - 项目类别:
New catalytic methods for the rapid synthesis of N-unprotected chiral aziridines and amines
快速合成N-未保护的手性氮丙啶和胺的新催化方法
- 批准号:
10782916 - 财政年份:2020
- 资助金额:
$ 32.07万 - 项目类别:
New catalytic methods for the rapid synthesis of N-unprotected chiral aziridines and amines
快速合成N-未保护的手性氮丙啶和胺的新催化方法
- 批准号:
10374006 - 财政年份:2020
- 资助金额:
$ 32.07万 - 项目类别:
Asymmetric N-H/N-alkyl olefin azirdinations and ring-opening transformations
不对称 N-H/N-烷基烯烃叠氮化和开环转化
- 批准号:
8865271 - 财政年份:2015
- 资助金额:
$ 32.07万 - 项目类别:
Asymmetric N-H/N-alkyl olefin azirdinations and ring-opening transformations
不对称 N-H/N-烷基烯烃叠氮化和开环转化
- 批准号:
9275107 - 财政年份:2015
- 资助金额:
$ 32.07万 - 项目类别:
Asymmetric N-H/N-alkyl olefin azirdinations and ring-opening transformations
不对称 N-H/N-烷基烯烃叠氮化和开环转化
- 批准号:
9064184 - 财政年份:2015
- 资助金额:
$ 32.07万 - 项目类别:
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