Strategies for the Catalytic Synthesis of Nitrogen-Containing Molecules
含氮分子的催化合成策略
基本信息
- 批准号:10405392
- 负责人:
- 金额:$ 38.44万
- 依托单位:
- 依托单位国家:美国
- 项目类别:
- 财政年份:2022
- 资助国家:美国
- 起止时间:2022-09-10 至 2027-06-30
- 项目状态:未结题
- 来源:
- 关键词:AlkylationAminesAreaCatalysisChemicalsComplexCouplingDevelopmentGoalsHealthHumanHydrogenIminesLaboratoriesMethodsNitrogenOrganic SynthesisOxidesPharmaceutical PreparationsPharmacologic SubstancePreparationProcessReactionReagentRouteSynthesis ChemistryUnited States National Institutes of HealthWorkbasecatalystcycloadditiondrug discoveryfallsfunctional grouphuman diseaseimprovedinnovationinventionnovelpyridinequinolinescaffoldsmall molecule
项目摘要
Project Abstract for NIH R35 (MIRA):
The discovery and development of new methods for the efficient synthesis of N-containing and F-containing
chemical building blocks is an important goal in organic synthesis as a large number of pharmaceuticals and
other bioactive molecules contain these atoms within a diverse set of chemical functional groups. More rapid
and/or selective assembly of known motifs, and moreover the preparation of new chemical landscapes, requires
innovative approaches to drug-like scaffolds, including the discovery of new reagents and new catalysts/catalytic
strategies.
The current goals of this project fall under three main focus areas. 1) We will develop 2-azatrienes, a novel class
of enamine umpolung reagents, for myriad catalytic enantioselective approaches towards chiral amines.
Representative reactions that will be developed include 6,3-, 6,5- and 5,6-hydrofunctionalizations including
reductive couplings with carbonyls and imines, hydroalkynylations, and hydroarylations. Azadienes generated
from 6,5- and 5,6-hydrofunctionalizations of the azatriene reagents may be utilized in myriad downstream
reactions, including other catalytic processes, thereby providing a diastereodivergent avenue towards highly
complex chiral amines through sequential catalysis. 2) We will expand upon our prior work in enantioselective
transformations of 2-azadienes, the first class of enamine umpolung reagents developed in our laboratory.
Examples include reductive couplings with aromatic heterocycles, such as quinoline N-oxides, catalytic
enantioselective fluorofunctionalizations with 4,4-difluoro-2-azadienes, cascade desymmetrization reactions,
and reductive [3+2]-cycloadditions. 3) We will develop catalytic remote C–C and C–B coupling reactions that
result in the loss of a halide from a trifluoromethyl group or H-atom abstraction from a difluoromethyl group to
deliver difluorocarbons in a number of settings. In one case, we will carry out borylation or enantioselective
alkylation of a 3-trifluoromethylpyridine scaffold to yield medicinally important and highly functionalized 3-
(difluoromethyl)pyridines. In another area, we will execute a radical hydrogen atom abstraction of 4-
difluoromethyl-2-azadienes to furnish a difluoro-2-azapentadienyl radical, which then may be engaged in
catalytic cross-couplings to furnish chiral allylic amines bearing a difluoroalkene unit.
Together, these undertakings will enable new chemical space for drug discovery to be obtained readily and with
great diversity from simple reagents. We will access more established N-containing motifs more quickly and with
greater levels of regio/stereocontrol compared to known approaches because of the invention of new reagents
and the novel reactivity that they embody.
NIH R35 (MIRA)项目摘要:
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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Steven Joseph Malcolmson其他文献
Steven Joseph Malcolmson的其他文献
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{{ truncateString('Steven Joseph Malcolmson', 18)}}的其他基金
Strategies for the Catalytic Synthesis of Nitrogen-Containing Molecules
含氮分子的催化合成策略
- 批准号:
10698004 - 财政年份:2022
- 资助金额:
$ 38.44万 - 项目类别:
A Reverse Polarity Stereoselective C-C Bond-Forming Strategy for Preparing Chiral Amines
制备手性胺的反极性立体选择性 C-C 键形成策略
- 批准号:
9975183 - 财政年份:2017
- 资助金额:
$ 38.44万 - 项目类别:
A Reverse Polarity Stereoselective C-C Bond-Forming Strategy for Preparing Chiral Amines
制备手性胺的反极性立体选择性 C-C 键形成策略
- 批准号:
9367817 - 财政年份:2017
- 资助金额:
$ 38.44万 - 项目类别:
A Reverse Polarity Stereoselective C-C Bond-Forming Strategy for Preparing Chiral Amines
制备手性胺的反极性立体选择性 C-C 键形成策略
- 批准号:
10217180 - 财政年份:2017
- 资助金额:
$ 38.44万 - 项目类别:
Probing the Biosynthesis of Thiazolyl Peptide Antibiotic Berninamycin A
噻唑基肽类抗生素伯尼霉素A的生物合成探讨
- 批准号:
8249239 - 财政年份:2012
- 资助金额:
$ 38.44万 - 项目类别:
Probing the Biosynthesis of Thiazolyl Peptide Antibiotic Berninamycin A
噻唑基肽类抗生素伯尼霉素A的生物合成探讨
- 批准号:
8426295 - 财政年份:2012
- 资助金额:
$ 38.44万 - 项目类别:
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