NEW METHODS FOR STEREOSELECTIVE ADDITIONS TO CARBONYLS

羰基立体选择性加成的新方法

基本信息

  • 批准号:
    2185974
  • 负责人:
  • 金额:
    $ 12.87万
  • 依托单位:
  • 依托单位国家:
    美国
  • 项目类别:
  • 财政年份:
    1993
  • 资助国家:
    美国
  • 起止时间:
    1993-07-01 至 1996-09-29
  • 项目状态:
    已结题

项目摘要

The long term objectives of this project are to develop new methods of asymmetric synthesis by gaining an understanding of the stereocontrol elements in existing methods, and applying what we have learned to the design of new reactions. We are primarily interested in reactions that form C-C bonds enantioselectively. Our approach focuses on the generation of chiral oxocarbenium ions, which can be considered activated ketones or aldehydes. these compounds may then undergo diastereoselective addition reactions, or Diels Alder reactions if the oxocarbenium ion is alpha-beta unsaturated, where the asymmetric induction is derived from the chirality of the oxocarbenium ion. In the first part of the proposal, we have unequivocally shown by a deuterium labeling experiment that the chiral acetal addition reactions discovered by W.S. Johnson proceed by way of an oxocarbenium ion. These reactions can display exceptional levels of diastereoselectivity, >300:1 in many cases, thus providing evidence that chiral oxocarbenium ions can provide high levels of asymmetric induction in addition reactions. We are extending our deuterated acetal studies to probe the mechanism of addition to acyclic acetals. We are also examining the activation of alpha-beta unsaturated carbonyl derivatives by their conversion to oxocarbenium ions. formation of the oxocarbenium ions in the Diels Alder reaction, allowing for new opportunities for controlling remote stereochemistry. We have proposed a short synthesis of the cholesterol biosynthesis inhibitor dihydrocompactin using this method, and are examining its scope. We also propose a catalytic variant where a chiral TMS ether is used in catalytic amounts to control the absolute stereochemistry in the Diels Alder reaction. Finally, we describe a chiral alpha-ferrocenyl cation which we hope will serve as an enantioselective catalyst for a variety of reactions. This reagent is similar to the trityl cation which has been shown to be an effective Lewis acid catalyst for numerous reactions including the aldol reaction, reduction of ketones with trialkylsilanes, 1,4 addition of silyl nucleophiles to alpha-beta unsaturated ketones and ester equivalents, and Diels Alder reactions. We describe an enantioselective synthesis of the catalyst precursor and have just begun to examine its reactivity as an asymmetric catalyst. The methods we discover can be used to synthesize a variety of molecules of medicinal interest.
这个项目的长期目标是开发新的方法

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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TAREK SAMMAKIA其他文献

TAREK SAMMAKIA的其他文献

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{{ truncateString('TAREK SAMMAKIA', 18)}}的其他基金

Glycoengineering of Therapeutic Peptides for Improved Treatment of Human Diseases
用于改善人类疾病治疗的治疗性肽的糖工程
  • 批准号:
    9977199
  • 财政年份:
    2018
  • 资助金额:
    $ 12.87万
  • 项目类别:
Glycoengineering of Therapeutic Peptides for Improved Treatment of Human Diseases
用于改善人类疾病治疗的治疗性肽的糖工程
  • 批准号:
    9754137
  • 财政年份:
    2018
  • 资助金额:
    $ 12.87万
  • 项目类别:
Glycoengineering of Therapeutic Peptides for Improved Treatment of Human Diseases
用于改善人类疾病治疗的治疗性肽的糖工程
  • 批准号:
    10212388
  • 财政年份:
    2018
  • 资助金额:
    $ 12.87万
  • 项目类别:
NEW METHODS FOR STEREOSELECTIVE ADDITIONS TO CARBONYLS
羰基立体选择性加成的新方法
  • 批准号:
    2185975
  • 财政年份:
    1993
  • 资助金额:
    $ 12.87万
  • 项目类别:
NEW METHODS FOR STEREOSELECTIVE ADDITIONS TO CARBONYLS
羰基立体选择性加成的新方法
  • 批准号:
    2546019
  • 财政年份:
    1993
  • 资助金额:
    $ 12.87万
  • 项目类别:
NEW METHODS FOR STEREOSELECTIVE ADDITIONS TO CARBONYLS
羰基立体选择性加成的新方法
  • 批准号:
    6519516
  • 财政年份:
    1993
  • 资助金额:
    $ 12.87万
  • 项目类别:
NEW METHODS FOR STEREOSELECTIVE ADDITIONS TO CARBONYLS
羰基立体选择性加成的新方法
  • 批准号:
    2796764
  • 财政年份:
    1993
  • 资助金额:
    $ 12.87万
  • 项目类别:
New Methods for Stereoselective Addictions to Carbonyls
羰基立体选择性成瘾的新方法
  • 批准号:
    7486841
  • 财政年份:
    1993
  • 资助金额:
    $ 12.87万
  • 项目类别:
NEW METHODS FOR STEREOSELECTIVE ADDITIONS TO CARBONYLS
羰基立体选择性加成的新方法
  • 批准号:
    6385778
  • 财政年份:
    1993
  • 资助金额:
    $ 12.87万
  • 项目类别:
NEW METHODS FOR STEREOSELECTIVE ADDITIONS TO CARBONYLS
羰基立体选择性加成的新方法
  • 批准号:
    2185973
  • 财政年份:
    1993
  • 资助金额:
    $ 12.87万
  • 项目类别:

相似国自然基金

Computational Methods for Analyzing Toponome Data
  • 批准号:
    60601030
  • 批准年份:
    2006
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    17.0 万元
  • 项目类别:
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