Recently developed organometallic complexes of Zn, Cu(Zn, Li), Fe, Ru and less-used ions. Use in selective 1,2- or 1,4-additions, transfer hydrogenations, aldol reactions and Diels-Alder reactions
Zhu, HJ; Jiang, JX; Ren, J; Yan, YM; Pittman, CU
2005-10-01
发表期刊CURRENT ORGANIC SYNTHESIS
卷号2期号:4页码:547-587
摘要This review introduces the broad general topic of asymmetric organic synthetic reactions and reagents. Reagents containing both frequently used metallic ions, e.g. Zn++, Cu+(++) and Ru++, and rarely used ions, such as Ag+, employed in the construction of designed chiral centers, are updated here. Enantioselective 1,2-additions and 1,4-conjugate additions, transfer hydrogenations, and diasteroselective aldol reaction are discussed. The selectivities induced by chiral beta-, delta- or gamma-chiral amino alcohols, chiral diols, chiral binaphthyl derivatives, chiral P,N-containing auxiliaries, and other ligands used to prepare chiral metallic complexes, were compared in each reaction system. The use of two or more metallic ions with a single chiral ligand has now become a more popular strategy to catalyze chiral-center-controlled processes. For example, only diethylzinc was used in enantioselective additions to aldchydes in early studies. Recently, the combination of Et2Zn and Cu++ in the selective additions has been used to achieve high ee% values and yields. Finally, quantum calculations have been used to obtain kinetic data to predict a reactions ee% values. For example, the calculated Delta G(cal). values have a strong relationship with the obtained Delta G(fit) values which have the direct linkage with the ee% values.
关键词Enantioselectivity Diastereoselectivity Conjugate Addition Aldol Reaction Hydrogenation Diels-alder
收录类别SCI
语种英语
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文献类型期刊论文
条目标识符http://ir.kib.ac.cn/handle/151853/14539
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, State Key Lab Phyytochem & Plant Resources, Kunming 650204, Yunnan, Peoples R China
2.Mississippi State Univ, Dept Chem, Mississippi State, MS 39762 USA
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Zhu, HJ,Jiang, JX,Ren, J,et al. Recently developed organometallic complexes of Zn, Cu(Zn, Li), Fe, Ru and less-used ions. Use in selective 1,2- or 1,4-additions, transfer hydrogenations, aldol reactions and Diels-Alder reactions[J]. CURRENT ORGANIC SYNTHESIS,2005,2(4):547-587.
APA Zhu, HJ,Jiang, JX,Ren, J,Yan, YM,&Pittman, CU.(2005).Recently developed organometallic complexes of Zn, Cu(Zn, Li), Fe, Ru and less-used ions. Use in selective 1,2- or 1,4-additions, transfer hydrogenations, aldol reactions and Diels-Alder reactions.CURRENT ORGANIC SYNTHESIS,2(4),547-587.
MLA Zhu, HJ,et al."Recently developed organometallic complexes of Zn, Cu(Zn, Li), Fe, Ru and less-used ions. Use in selective 1,2- or 1,4-additions, transfer hydrogenations, aldol reactions and Diels-Alder reactions".CURRENT ORGANIC SYNTHESIS 2.4(2005):547-587.
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