New Aryl and Vinyl Amination Methods
新的芳基和乙烯基胺化方法
基本信息
- 批准号:6624259
- 负责人:
- 金额:$ 24.55万
- 依托单位:
- 依托单位国家:美国
- 项目类别:
- 财政年份:2002
- 资助国家:美国
- 起止时间:2002-03-01 至 2007-04-30
- 项目状态:已结题
- 来源:
- 关键词:
项目摘要
DESCRIPTION: (provided by applicant) This proposal describes free
radical-mediated aryl and vinyl amination reactions to synthesize indoline and
pyrrolidine heterocycles, respectively. By virtue of the pH-neutral conditions
involved, this technology is superior to most alternative methods by measures
of chemoselectivity. The strategy differs conceptually in that activation of a
nitrogen carbon pi bond in the amine is involved instead of nitrogen-hydrogen
sigma bond activation. To accomplish amination, carbon radicals are
regioselectively added to the nitrogen of the azomethine. In so far as carbon
radicals are known to add efficiently to the carbon of a variety of
azomethinecontaining functional groups, the additions described are highly
nonconventional and nearly without precedent. The mild reaction conditions are
uniquely well-suited to transformations of structurally complex and highly
functionalized intermediates used in target-oriented synthesis. The use of
radical intermediates also allows development of tandem bond-forming processes.
The development of radical-mediated aryl amination is extended to convergent
indoline annulation strategies. These processes are unique in their ability to
enantioselectively construct indoline heterocycles, including alpha-amino
acids. To illustrate some of the important characteristics of this method, a
total synthesis is proposed of a member of the ambiguine indole alkaloids for
which no synthesis route exists.
The development of free radical-mediated vinyl amination includes use of the
enamine products as intermediates toward functionalized pyrrolidines. The
importance of these pyrrolidinyl enamines is demonstrated by the convergent and
concise synthesis of nat-mitomycin C for which no enantioselective synthesis
currently exists.
描述:(由申请人提供)本提案描述了免费
自由基介导的芳基和乙烯基胺化反应合成吲哚啉,
吡咯烷杂环。由于pH中性条件
从测量结果来看,该技术比大多数替代方法都要上级
化学选择性。该策略在概念上的不同之处在于,
胺中的氮碳π键代替氮-氢参与
σ键活化为了完成胺化,碳自由基被
区域选择性地加到甲亚胺的氮上。至于碳,
已知自由基有效地添加到各种
由于含有偶氮甲环的官能团,所述的加成是高度
非常规的,几乎没有先例的。温和的反应条件为:
特别适合于结构复杂和高度复杂的
用于靶向合成的官能化中间体。使用
自由基中间体还允许开发串联键形成过程。
自由基介导的芳基胺化反应的发展扩展到收敛
吲哚啉环化策略。这些过程的独特之处在于,
对映选择性地构建二氢吲哚杂环,包括α-氨基
acids.为了说明此方法的一些重要特性,
提出了一种新的吲哚生物碱的全合成方法,
不存在合成路线。
自由基介导的乙烯基胺化的发展包括使用
烯胺产物作为制备官能化吡咯烷的中间体。的
这些吡咯烷基烯胺的重要性通过会聚和
不存在对映选择性的nat-丝裂霉素C的简便合成
目前存在。
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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Jeffrey Nicholas Johnston其他文献
Jeffrey Nicholas Johnston的其他文献
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{{ truncateString('Jeffrey Nicholas Johnston', 18)}}的其他基金
Development of a Mirror-Image Natural Product as an Antiarrhythmic Therapeutic
开发镜像天然产物作为抗心律失常疗法
- 批准号:
10589858 - 财政年份:2020
- 资助金额:
$ 24.55万 - 项目类别:
Development of a Mirror-Image Natural Product as an Antiarrhythmic Therapeutic
开发镜像天然产物作为抗心律失常疗法
- 批准号:
10372134 - 财政年份:2020
- 资助金额:
$ 24.55万 - 项目类别:
Development of a Mirror-Image Natural Product as an Antiarrhythmic Therapeutic
开发镜像天然产物作为抗心律失常疗法
- 批准号:
9917405 - 财政年份:2020
- 资助金额:
$ 24.55万 - 项目类别:
New Stereoselective Reactions for Chiral Amine Synthesis
手性胺合成的新立体选择性反应
- 批准号:
8110644 - 财政年份:2009
- 资助金额:
$ 24.55万 - 项目类别:
Enantioselective Functionalizations of Azomethines and Alkenes
甲亚胺和烯烃的对映选择性官能化
- 批准号:
9050686 - 财政年份:2009
- 资助金额:
$ 24.55万 - 项目类别:
Enantioselective Functionalizations of Azomethines and Alkenes
甲亚胺和烯烃的对映选择性官能化
- 批准号:
8697731 - 财政年份:2009
- 资助金额:
$ 24.55万 - 项目类别:
New Stereoselective Reactions for Chiral Amine Synthesis
手性胺合成的新立体选择性反应
- 批准号:
8267696 - 财政年份:2009
- 资助金额:
$ 24.55万 - 项目类别:
New Stereoselective Reactions for Chiral Amine Synthesis
手性胺合成的新立体选择性反应
- 批准号:
7817116 - 财政年份:2009
- 资助金额:
$ 24.55万 - 项目类别: