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 |
| DOI | 10.1002/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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