Design of novel functional oxide and its application to catalytic reactions
新型功能氧化物的设计及其在催化反应中的应用
基本信息
- 批准号:16590001
- 负责人:
- 金额:$ 2.18万
- 依托单位:
- 依托单位国家:日本
- 项目类别:Grant-in-Aid for Scientific Research (C)
- 财政年份:2004
- 资助国家:日本
- 起止时间:2004 至 2005
- 项目状态:已结题
- 来源:
- 关键词:
项目摘要
Organocatalysis has been one of the current hot topics in the field of synthetic chemistry because of its environmentally benign nature. Recently, asymmetric organocatalyses utilizing neutral Lewis bases attracted much attention because it led to the emergence of new types of chiral ligands based on functional oxide compounds. Phosphine oxide has high polarity and relatively low Bronsted basicity, whose reactivity is expected to be similar to those of such Lewis bases. Moreover, various types of chiral phosphine oxides can be easily obtained by the simple oxidation of commercially available chiral phosphines. However, the examples of the application of chiral phosphine oxides to asymmetric organocatalyses are still limited. We investigated the catalytic activity of BINAPO, which is easily prepared from the most common chiral phosphine ligand BINAP. We found that BINAPO was an effective catalyst for the enantioselective allylation of aldehyde with allyltrichlorosilane and the enantiosel … More ective aldol reaction of trichlorosilyl enol, wherein the allylated adducts or aldol adducts were obtained in high diastereo- and enantioselectivities (up tp 96% ee). BINAPO was found to be effective in the enantioselective ring opening of meso-epoxides with tetrachlorosilane in the presence of diisopropylethylamine, affording the corresponding chlorohydrins in high enantioselectivities of up to 90% ee. An aldol reaction of trimethoxysilyl enol ether catalyzed by lithium binaphthoxide was also developed. The aldol reaction of trimethoxysilyl enol ether derived from cyclohexanone under anhydrous conditions predominantly afforded the anti-aldol adduct with moderate enantioselectivity, whereas the reaction under hydrous conditions predominantly resulted in the syn-adduct and the enantioselectivity of the syn-adduct was considerably improved. The best enantioselectivity was obtained in the reaction of trimethoxysilyl enol ether derived from 1-indanone with cyclohexanecarboxaldehyde (97% ee (syn)). This is the first example of an aldol reaction of trimethoxysilyl enol ether catalyzed by a chiral base. Less
有机催化因其对环境友好的特性,成为当前合成化学领域的研究热点之一。近年来,利用中性刘易斯碱合成的不对称有机催化剂引起了人们的广泛关注,因为它导致了基于功能氧化物的新型手性配体的出现。氧化膦具有高极性和相对低的布朗斯台德碱度,预期其反应性类似于这些刘易斯碱。此外,各种类型的手性氧化膦可以通过简单氧化市售手性膦容易地获得。然而,手性氧化膦在不对称有机催化中的应用实例仍然有限。我们研究了BINAPO的催化活性,它很容易从最常见的手性膦配体BINAP制备。我们发现BINAPO是一种有效的催化剂,可用于醛与烯丙基三氯硅烷的不对称烯丙基化反应, ...更多信息 三氯甲硅烷基烯醇的有效Aldol反应,其中烯丙基化的加合物或Aldol加合物以高的非对映体和对映体选择性(高达96%ee)获得。在二异丙基乙胺存在下,BINAPO能有效地催化四氯硅烷对映体的开环反应,生成相应的氯代醇,其对映体选择性高达90%ee.环己酮衍生的三甲氧基硅烯醇醚在无水条件下的Aldol反应主要得到具有中等对映选择性的反Aldol加合物,而在含水条件下的反应主要得到合成加合物,并且合成加合物的对映选择性显著提高。由1-茚酮衍生的三甲氧基硅烯醇醚与环己烷甲醛的反应具有最好的对映选择性(97%ee(syn))。这是手性碱催化的三甲氧基甲硅烷基烯醇醚的羟醛缩合反应的第一个例子。少
项目成果
期刊论文数量(29)
专著数量(0)
科研奖励数量(0)
会议论文数量(0)
专利数量(0)
Asymmetric ring opening of meso-epoxides catalyzed by the chiral phosphine oxide BINAPO
- DOI:10.1016/j.tetasy.2005.06.021
- 发表时间:2005-07-18
- 期刊:
- 影响因子:0
- 作者:Tokuoka, E;Kotani, S;Nakajima, M
- 通讯作者:Nakajima, M
Enantioselective aldol reactions of trichlorosilyl enol ethers catalyzed by chiral N,N′-dioxides and monodentate N-oxides
- DOI:10.1016/j.tetlet.2003.10.114
- 发表时间:2004
- 期刊:
- 影响因子:1.8
- 作者:M. Nakajima;T. Yokota;M. Saito;S. Hashimoto*
- 通讯作者:M. Nakajima;T. Yokota;M. Saito;S. Hashimoto*
Enantioselective aldol reactions of trichlorosilyl enol ethers catalyzed by the chiral phosphine oxide BINAPO
- DOI:10.1055/s-2006-939725
- 发表时间:2006-05-03
- 期刊:
- 影响因子:2
- 作者:Kotani, Shunsuke;Hashimoto, Shunichi;Nakajima, Makoto
- 通讯作者:Nakajima, Makoto
The Enantioselective Aldol Reaction of Trimethoxysilyl Enol Ether Catalyzed by Lithium Binaphtholate.
联萘酸锂催化三甲氧基硅烯醇醚的对映选择性羟醛反应。
- DOI:
- 发表时间:2004
- 期刊:
- 影响因子:0
- 作者:Nakajima;M.;Orito;Y.;Ishizuka;T.;Hashimoto;S.
- 通讯作者:S.
Chiral Phosphine Oxide as a Catalyst for Enantioselective Allylation of Aldehydes with Allyltrichlorosilane.
手性氧化膦作为醛与烯丙基三氯硅烷对映选择性烯丙基化的催化剂。
- DOI:
- 发表时间:2005
- 期刊:
- 影响因子:0
- 作者:Nakajima;M.;Kotani;S.;Ishizuka;T.;Hashimoto;S.
- 通讯作者:S.
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NAKAJIMA Makoto其他文献
NAKAJIMA Makoto的其他文献
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{{ truncateString('NAKAJIMA Makoto', 18)}}的其他基金
Pathological mechanism of intracranial dolichoectasia -to resolve the dilemma in antithrombotic treatment
颅内细长扩张症的病理机制——破解抗栓治疗困境
- 批准号:
25893185 - 财政年份:2013
- 资助金额:
$ 2.18万 - 项目类别:
Grant-in-Aid for Research Activity Start-up
Nearfield magnetic effect of THz pulses and magnetic THz imaging
太赫兹脉冲的近场磁效应和磁太赫兹成像
- 批准号:
24656043 - 财政年份:2012
- 资助金额:
$ 2.18万 - 项目类别:
Grant-in-Aid for Challenging Exploratory Research
Immunohistochemical study of relationship between autophagy marker LC3 and nutritional state in human livers.
自噬标记物 LC3 与人肝脏营养状态关系的免疫组织化学研究。
- 批准号:
24590851 - 财政年份:2012
- 资助金额:
$ 2.18万 - 项目类别:
Grant-in-Aid for Scientific Research (C)
Observation of ultrafast spin dynamics using by half-cycled THz pulses
使用半周期太赫兹脉冲观察超快自旋动力学
- 批准号:
23686012 - 财政年份:2011
- 资助金额:
$ 2.18万 - 项目类别:
Grant-in-Aid for Young Scientists (A)
Study of the ultrafast dynamics of photo-induced insulator-metal transition using terahertz pulses
使用太赫兹脉冲研究光致绝缘体-金属转变的超快动力学
- 批准号:
21760004 - 财政年份:2009
- 资助金额:
$ 2.18万 - 项目类别:
Grant-in-Aid for Young Scientists (B)
Development of Novel Catalyses Based on Base-Activated Silicates
基于碱活化硅酸盐的新型催化剂的开发
- 批准号:
18590007 - 财政年份:2006
- 资助金额:
$ 2.18万 - 项目类别:
Grant-in-Aid for Scientific Research (C)
Development of new function of N-oxide based on the electron-donating property of oxide oxygen
基于氧化物氧的给电子特性开发N-氧化物新功能
- 批准号:
13672204 - 财政年份:2001
- 资助金额:
$ 2.18万 - 项目类别:
Grant-in-Aid for Scientific Research (C)
A study on the regional structure of the Yoshinogawa drainage by GIS(Geographical Information System) methods
吉野川流域区域结构的GIS(地理信息系统)研究
- 批准号:
13490020 - 财政年份:2001
- 资助金额:
$ 2.18万 - 项目类别:
Grant-in-Aid for Scientific Research (B)
アミン-N-オキシドを触媒とする新規不斉合成反応の開発
使用胺-N-氧化物作为催化剂开发新型不对称合成反应
- 批准号:
10671978 - 财政年份:1998
- 资助金额:
$ 2.18万 - 项目类别:
Grant-in-Aid for Scientific Research (C)
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