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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
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)
2006
发表期刊Organometallics
ISSN0276-7333
卷号25期号:7页码:1676-1688
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.
学科领域金属有机化学
部门归属上海有机所; 香港大学
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收录类别SCI
语种英语
WOS记录号WOS:000236288100019
引用统计
被引频次:29[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/27645
专题上海有机化学研究所
通讯作者Zhi ZM(支志明)
推荐引用方式
GB/T 7714
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.
APA 李功勇,张静,陈伟雄,徐镇江,朱年勇,&支志明.(2006).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.Organometallics,25(7),1676-1688.
MLA 李功勇,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".Organometallics 25.7(2006):1676-1688.
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