Unexpected selectivity in sodium borohydride reductions of alpha-substituted esters: Experimental and theoretical studies
文献类型：期刊论文
| 作者 | Li, LC; Jiang, JX; Ren, J; Ren, Y; Pittman, CU; Zhu, HJ |
| 刊名 | EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
 |
| 出版日期 | 2006-04-10 |
| 期号 | 8页码:1981-1990 |
| 关键词 | Borohydrides Chemoselectivity Density Functional Calculations Esters Reduction |
| ISSN号 | 1434-193X |
| DOI | 10.1002/ejoc.200500824 |
| 通讯作者 | hjzhu@mail.kib.ac.cn |
| 文献子类 | Article |
| 英文摘要 | The propensity of sodium borohydride to reduce the carbonyl group in eleven alpha-substituted and two aromatic esters has been investigated by experiments and at the B3LYP/631++G(d,p)//HF/6-3lG(d,p) level of theory. The chemoselectivities in nine of these reductions have been examined by experiments. Experimental results agree well with the calculated order of activation energies for hydride transfer to the ester carbonyl group. Methyl a-bromoacetate reduces faster than methyl a-fluoroacetate. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006). |
| 学科主题 | Chemistry, Organic |
| WOS关键词 | INCL3-NABH4 REAGENT SYSTEM ; CARBOXYLIC-ACIDS ; CHEMOSELECTIVE REDUCTIONS ; CONJUGATED KETONES ; CARBONYL-COMPOUNDS ; ORGANIC-SYNTHESIS ; DIELECTRIC MODEL ; IONIC-SOLUTIONS ; AMINO-ACIDS ; BETA-KETO |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000236838800020 |
| 公开日期 | 2011-12-19 |
| 源URL | [http://ir.kib.ac.cn:8080/handle/151853/2847]  |
| 专题 | 昆明植物研究所_植物化学与西部植物资源持续利用国家重点实验室 |
| 作者单位 | 1.CAS, Kunming Inst Bot, Organ Synth & Nat Prod Lab, Kunming 650204, Peoples R China 2.Mississippi State Univ, Dept Chem, Mississippi State, MS 39762 USA 3.Mississippi State Univ, Dept Chem, Mississippi State, MS 39762 USA 4.Sichuan Univ, Coll Chem, Chengdu 610064, Peoples R China 5.Chinese Acad Sci, Grad Sch, Beijing 100039, Peoples R China |
| 推荐引用方式 GB/T 7714 | Li, LC,Jiang, JX,Ren, J,et al. Unexpected selectivity in sodium borohydride reductions of alpha-substituted esters: Experimental and theoretical studies[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,2006(8):1981-1990. |
| APA | Li, LC,Jiang, JX,Ren, J,Ren, Y,Pittman, CU,&Zhu, HJ.(2006).Unexpected selectivity in sodium borohydride reductions of alpha-substituted esters: Experimental and theoretical studies.EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(8),1981-1990. |
| MLA | Li, LC,et al."Unexpected selectivity in sodium borohydride reductions of alpha-substituted esters: Experimental and theoretical studies".EUROPEAN JOURNAL OF ORGANIC CHEMISTRY .8(2006):1981-1990. |
入库方式： OAI收割
来源：昆明植物研究所
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