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
- 来源:
- 关键词:
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:
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