Unexpected selectivity in sodium borohydride reductions of alpha-substituted esters: Experimental and theoretical studies

doi:10.1002/ejoc.200500824

	Unexpected selectivity in sodium borohydride reductions of alpha-substituted esters: Experimental and theoretical studies
	Li, LC ; Jiang, JX ; Ren, J ; Ren, Y ; Pittman, CU ; Zhu, HJ
通讯作者	hjzhu@mail.kib.ac.cn
	2006-04-10
发表期刊	EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN	1434-193X
期号	8 页码:1981-1990
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).
关键词	Borohydrides Chemoselectivity Density Functional Calculations Esters Reduction
学科领域	Chemistry, Organic
DOI	10.1002/ejoc.200500824
收录类别	SCI
语种	英语
WOS记录号	WOS:000236838800020
引用统计
文献类型	期刊论文
条目标识符	http://ir.kib.ac.cn/handle/151853/2847
专题	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.

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