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学科主题: 金属有机化学
题名: Enantioselective intramolecular cyclopropanation of cis-alkenes by chiral ruthenium(II) Schiff base catalysts and crystal structures of (Schiff base)ruthenium complexes containing carbene, PPh3, and CO ligands
其他题名: 手性钌席夫碱络合物结构及其催化的分子内环丙烷化反应的研究
作者: Li GY(李功勇) ; Zhang J(张静) ; Chen WX(陈伟雄) ; Xu ZJ(徐镇江) ; Zhu NY(朱年勇) ; Zhi ZM(支志明)
通讯作者: 支志明
刊名: Organometallics
发表日期: 2006
卷: 25, 期:7, 页:1676-1688
收录类别: SCI
部门归属: 上海有机所; 香港大学
英文摘要: The enantioselective intramolecular cyclopropanation of cis-substituted allylic diazoacetates catalyzed by the chiral ruthenium Schiff base complexes [RU(Schiff base)(PPh(3)h] (1) is described. Among this class of complexes examined, [Ru(2-Br-salen)(PPh3)(2)] (1a) is the most effective, catalyzing intramolecular cyclopropanation of cis-allylic diazoacetates cis-(CRH=CH)CH2OC(O)CHN2, (R = alkyl, aryl) in CHCl3 solution to give [3.1.0.]-bicyclic lactones with yields and ee values up to 71 and 90%, respectively. The analogous reactions of cis-alkenyl diazoacetates using [Ru(Schiff base)(CO)] (2) as catalyst gave comparable enantioselectivities (up to 91% ee) but lower product yields of 20-38%. Treatment of [Ru(2,4-X-salen)(PPh3)(2)] (1d, X = Br; 1e, X = Cl; 1f, X = 1) with N2C(p-YC6H4)(2) (Y = H, MeO) and N-methylimidazole (MeIm) or pyridine (py) gave the monocarbene complexes [Ru(2,4-X-salen)(C(pYC(6)H(4))(2))(MeIm)] (3a, X = Br, Y = H; 3b, X = Cl, Y = H; 3c, X = I, Y = H; 3d, X = Br, Y = OMe) and [Ru(2,4-Br-salen)(CPh2)(py)] (4, H-2(2,4-Br-salen) = bis(3,5-dibromosalicylidene)-(1R,2R)-cyclo-hexanediamine), respectively. X-ray crystal structure determinations revealed Ru=C(carbene) distances of 1.921(12) angstrom for 3a, 1.913(5) angstrom for 3b, 1.919(14) angstrom for 3c, 1.910(2) angstrom for 3d, and 1.917(4) angstrom for 4. A comparison of the structures and electrochemistry of 1, [Ru(Schiff base) (CO) (MeIm)], 3, and 4 with those of the porphyrin analogues is presented.
语种: 英语
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WOS记录号: WOS:000236288100019
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/27645
Appears in Collections:上海有机化学研究所_期刊论文

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Recommended Citation:
Li GY,Zhang J,Chen WX,et al. Enantioselective intramolecular cyclopropanation of cis-alkenes by chiral ruthenium(II) Schiff base catalysts and crystal structures of (Schiff base)ruthenium complexes containing carbene, PPh3, and CO ligands[J]. Organometallics,2006,25(7):1676-1688.
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