Chiral N,N′-dioxide-iron(II) complexes catalyzed enantioselective oxa-Michael addition of α,β-unsaturated aldehydes

Chang, Lu; Shang, Deju; Xin, Junguo; Liu, Xiaohua; Feng, Xiaoming

doi:10.1016/j.tetlet.2008.09.041

Cited by 25 publications

(9 citation statements)

References 47 publications

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“…These Oalkylated oximes were isolated in 30−62% yields and 72−76% ee (Scheme 22). 160 The yield of 44 was reduced when the aldehydes possessed sterically hindered substituents R, whereas these substituents did not significantly affect the enantiomeric composition of 44. 160 The addition of any one of the acids was necessary to increase the yields of 44.…”

Section: Metal-mediated Reactions Of the Oxime Groupmentioning

confidence: 98%

Metal-Involving Synthesis and Reactions of Oximes

et al. 2017

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This review classifies and summarizes the past 10-15 years of advancements in the field of metal-involving (i.e., metal-mediated and metal-catalyzed) reactions of oximes. These reactions are diverse in nature and have been employed for syntheses of oxime-based metal complexes and cage-compounds, oxime functionalizations, and the preparation of new classes of organic species, in particular, a wide variety of heterocyclic systems spanning small 3-membered ring systems to macroheterocycles. This consideration gives a general outlook of reaction routes, mechanisms, and driving forces and underlines the potential of metal-involving conversions of oxime species for application in various fields of chemistry and draws attention to the emerging putative targets.

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Section: Metal-mediated Reactions Of the Oxime Groupmentioning

confidence: 98%

Metal-Involving Synthesis and Reactions of Oximes

et al. 2017

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“…Since the first example of catalytic asymmetric intermolecular oxa-Michael addition was disclosed by the Jacobsen group using (salen)aluminum catalysts in 2004, Feng and co-workers described an asymmetric intramolecular oxa-Michael addition of the phenol group to activated enones catalyzed by chiral complexes L20d –Ni(II) (Scheme a), generating the corresponding enantiopure flavanones in 90–99% yields and 80–99% ee’s. Later studies showed that the chiral N,N′ -dioxide – iron(II) complexes ( L21e –Fe) could be successfully applied to the intermolecular oxa-Michael addition of oximes to α,β-unsaturated aldehydes, which led to the corresponding adducts in moderate to good yield with up to 76% ee (Scheme b) …”

Section: C–heteroatom Bond Formation By Metal-catalyzed Aca Reactionsmentioning

confidence: 99%

“…Later studies showed that the chiral N,N′dioxide−iron(II) complexes (L21e−Fe) could be successfully applied to the intermolecular oxa-Michael addition of oximes to α,β-unsaturated aldehydes, which led to the corresponding adducts in moderate to good yield with up to 76% ee (Scheme 86b). 348 In terms of oxygen nucleophiles, water would be the best choice. The direct enantioselective 1,4-addition of water to α,β-unsaturated acceptors is a significant challenge in asymmetric catalysis.…”

Section: Conjugate Addition Of Oxygen Nucleophilesmentioning

confidence: 99%

Recent Advances in Metal-Catalyzed Asymmetric 1,4-Conjugate Addition (ACA) of Nonorganometallic Nucleophiles

2018

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The metal-catalyzed asymmetric conjugate addition (ACA) reaction has emerged as a general and powerful approach for the construction of optically active compounds and is among the most significant and useful reactions in synthetic organic chemistry. In recent years, great progress has been made in this area with the use of various chiral metal complexes based on different chiral ligands. This review provides comprehensive and critical information on the enantioselective 1,4-conjugate addition of nonorganometallic (soft) nucleophiles and their importance in synthetic applications. The literature is covered from the last 10 years, and a number of examples from before 2007 are included as background information. The review is divided into multiple parts according to the type of nucleophile involved in the reaction (such as C-, B-, O-, N-, S-, P-, and Si-centered nucleophiles) and metal catalyst systems used.

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“…Recently, iron complex has been used for several organic transformations such as the epoxidation of styrene [15], oxidation of alcohol [16][17], asymmetric synthesis [18][19][20], amination [21], and also for the Michael addition reactions [22][23]. However, optical properties of the metal complexes contain an interesting area of semiconducting along with optical materials because -CH=N group is isoelectronic with the -CH=CH group in these metal complexes with the incorporation of nitrogen atoms into the conjugated system.…”

Section: Introductionmentioning

confidence: 99%

Imidazolium supported iron-chloroglycine complex, a good turnover recyclable catalyst for the solvent free synthesis of 3, 4-dihydropyrimidin-2(1H)-ones – promoted by ultrasound irradiation

et al. 2019

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Abstract. A novel large band gap 1-glycyl-3-methyl imidazolium chloride-iron (III) complex [[Gmim]Cl-Fe(III)] was found to be a heterogeneous catalyst for an efficient and solvent free synthesis of 3,4-dihydropyrimidin-2(1H)-ones by condensation of substituted aldehydes, ethyl acetoacetate and urea (or) thiourea with tremendous yields in high turnover number (4.1X102 to 18.8X102) at ambient temperature using ultrasound irradiation as the activation mode of reaction. This operation formulates very interesting, ecological perspective due to simple reaction condition, isolation and purification of products. In addition, this methodology offers a competitive recyclability of the catalyst without a significant loss of its catalytic activity and could be readily reused, thus making this protocol more environmentally acceptable whilst no catalyst leaching was observed. Resumen. Se descubrió que un complejo novedoso de banda ancha 1-glicil-3-metilimidazolio cloruro de hierro (III) [[Gmim] Cl-Fe (III)] es un catalizador heterogéneo para una síntesis eficiente y libre de solventes de 3,4- dihidropirimidin-2 (1H) -ones por condensación de aldehídos sustituidos, acetoacetato de etilo y tiourea urea (o) con tremendos rendimientos en alto número de recambio (4.1X102 a 18.8X102) a temperatura ambiente mediante irradiación con ultrasonido como modo de activación de reacción. Esta operación formula una perspectiva ecológica muy interesante debido a la condición de reacción simple, el aislamiento y la purificación de los productos. Además, esta metodología ofrece una reciclabilidad competitiva del catalizador sin una pérdida significativa de su actividad catalítica y podría reutilizarse fácilmente, lo que hace que este protocolo sea más aceptable para el medio ambiente sin que se observe lixiviación del catalizador.

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Chiral N,N′-dioxide-iron(II) complexes catalyzed enantioselective oxa-Michael addition of α,β-unsaturated aldehydes

Cited by 25 publications

References 47 publications

Metal-Involving Synthesis and Reactions of Oximes

Metal-Involving Synthesis and Reactions of Oximes

Recent Advances in Metal-Catalyzed Asymmetric 1,4-Conjugate Addition (ACA) of Nonorganometallic Nucleophiles

Imidazolium supported iron-chloroglycine complex, a good turnover recyclable catalyst for the solvent free synthesis of 3, 4-dihydropyrimidin-2(1H)-ones – promoted by ultrasound irradiation

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