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题名: Unexpected selectivity in sodium borohydride reductions of alpha-substituted esters: Experimental and theoretical studies
作者: Li, LC; Jiang, JX; Ren, J; Ren, Y; Pittman, CU; Zhu, HJ
刊名: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
关键词: borohydrides ; chemoselectivity ; density functional calculations ; esters ; reduction
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).
出版日期: 2006-04-10
期号: 8, 页码:1981-1990
DOI标识: 10.1002/ejoc.200500824
语种: 英语
收录类别: SCI
学科分类: Chemistry, Organic
ISSN号: 1434-193X
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.kib.ac.cn/handle/151853/2847
Appears in Collections:植物化学与西部植物资源持续利用国家重点实验室_期刊论文

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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

Recommended Citation:
Li, LC; Jiang, JX; Ren, J; Ren, Y; Pittman, CU; Zhu, HJ.Unexpected selectivity in sodium borohydride reductions of alpha-substituted esters: Experimental and theoretical studies,EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,2006,(8):1981-1990
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