中国科学院机构知识库网格
Chinese Academy of Sciences Institutional Repositories Grid
Organocatalyzed highly enantioselective direct aldol reactions of aldehydes with hydroxyacetone and fluoroacetone in aqueous media: the use of water to control regioselectivity

文献类型:期刊论文

作者Chen, Xiao-Hua; Luo, Shi-Wei; Tang, Zhuo; Cun, Lin-Feng; Mi, Ai-Qiao; Jiang, Yao-Zhong; Gong, Liu-Zhu
刊名Chemistry-a european journal
出版日期2007
卷号13期号:2页码:689-701
关键词Aldol reaction Green chemistry Organocatalysis Proline amides Regioselectivity
ISSN号0947-6539
DOI10.1002/chem.200600801
通讯作者Gong, liu-zhu(gonglz@ustc.edu.cn)
英文摘要An organocatalyst prepared from (2r,3r)-diethyl 2-amino-3-hydroxysuccinate and l-proline exhibited high regio- and enantioselectivities for the direct aldol reactions of hydroxyacetone and fluoroacetone with aldehydes in aqueous media. it was found that water could be used to control the regioselectivity. the presence of 20-30 mol % of the catalyst afforded the direct aldol reactions of a wide range of aldehydes with hydroxyacetone to give the otherwise disfavored products with excellent enantioselectivities, ranging from 91 to 99 % ee, and high regioselectivities. aldolizations of fluoroacetone with aldehydes mediated by 30 mol% of the organocatalyst in aqueous media preferentially occurred at the methyl group, yielding products with high enantioselectivities (up to 91% ee); however, these additions took place dominantly at the fluoromethyl group in the optically active 3,5-disubstituted tetrahydrofurans and (2s,4r)-dihydroxy-4-biphenylbutyric acid were prepared by starting from the aldol reaction of hydroxyacetone. theoretical studies on the role of water in controlling the regioselectivity revealed that the hydrogen bonds formed between the amide oxygen of proline amide, the hydroxy of hydroxyacetone, and water are responsible for the regioselectivity by microsolvation with explicit one water molecule as a hydrogen-bond donor and/or an acceptor.
WOS关键词CATALYTIC ASYMMETRIC ALDOL ; PHASE-TRANSFER CATALYSIS ; DE-NOVO SYNTHESIS ; AMINO-ACID ; IONIC LIQUID ; ORGANIC-REACTIONS ; UNPRECEDENTED REGIOCONTROL ; BETA-HYDROXYKETONES ; 2-STEP SYNTHESIS ; PROLINE
WOS研究方向Chemistry
WOS类目Chemistry, Multidisciplinary
语种英语
WOS记录号WOS:000243519000034
出版者WILEY-V C H VERLAG GMBH
URI标识http://www.irgrid.ac.cn/handle/1471x/2380376
专题中国科学院大学
通讯作者Gong, Liu-Zhu
作者单位1.Chinese Acad Sci, Key Lab Asymmetr Synth & Chirotechnol Sichuan Pro, Chengdu Inst Organ Chem, Chengdu 610064, Peoples R China
2.Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Peoples R China
3.Univ Sci & Technol China, Dept Chem, Hefei 230026, Peoples R China
4.Chinese Acad Sci, Grad Sch, Beijing, Peoples R China
推荐引用方式
GB/T 7714
Chen, Xiao-Hua,Luo, Shi-Wei,Tang, Zhuo,et al. Organocatalyzed highly enantioselective direct aldol reactions of aldehydes with hydroxyacetone and fluoroacetone in aqueous media: the use of water to control regioselectivity[J]. Chemistry-a european journal,2007,13(2):689-701.
APA Chen, Xiao-Hua.,Luo, Shi-Wei.,Tang, Zhuo.,Cun, Lin-Feng.,Mi, Ai-Qiao.,...&Gong, Liu-Zhu.(2007).Organocatalyzed highly enantioselective direct aldol reactions of aldehydes with hydroxyacetone and fluoroacetone in aqueous media: the use of water to control regioselectivity.Chemistry-a european journal,13(2),689-701.
MLA Chen, Xiao-Hua,et al."Organocatalyzed highly enantioselective direct aldol reactions of aldehydes with hydroxyacetone and fluoroacetone in aqueous media: the use of water to control regioselectivity".Chemistry-a european journal 13.2(2007):689-701.

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来源:中国科学院大学

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