Aluminum-Controlled Reactivity and Diastereoselectivity toward Radical Reactions of Optically Active Aldimines with Metallic Samarium

Yanada, Reiko; Okaniwa, Masanori; Kaieda, Akira; Ibuka, Toshiro; Takemoto, Yoshiji

doi:10.1021/jo0014616

Cited by 34 publications

(13 citation statements)

References 25 publications

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“…Alternatively, the imine can be activated with trimethylaulminium, provided a free hydroxyl group is present in the auxiliary (Scheme 40). Under these conditions the same asymmetric induction with respect to the indiumcatalyzed reaction is observed [63].…”

Section: Samariumsupporting

confidence: 58%

Stereoselective Allylation Reactions of Imines and Related Compounds

Merino¹,

Tejero²,

Delso³

et al. 2005

COS

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The stereoselective allylation of imines and related compounds is one of the most effective methods for the introduction of an amino group into carbon skeletons. Moreover, by extending the process to other C=N functionalities such as oximes, hydrazones, nitrones and iminium ions, a variety of nitrogen-containing functional groups can be prepared with the concomitant introduction of the allyl moiety. In several instances it is possible to achieve a complete stereocontrol by using different organometallic reagents. In other cases, either the protective group tuning or the reaction time is crucial for the stereoselectivity of the reaction. This review covers the evolution of stereoselective allylation of imines and related compounds, including oximes, hydrazones, nitrones and iminium ions, from the use of allylic organometallic reagents over chiral substrates up to the recent development of enantioselective methods.

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Section: Samariumsupporting

confidence: 58%

Stereoselective Allylation Reactions of Imines and Related Compounds

Merino¹,

Tejero²,

Delso³

et al. 2005

COS

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“…7H 2 O) [21]. Recently, Yanada and co-workers reported the diastereoselective Barbier type allylation of the methyl N-benzylidene-(S)-valinol with allyl halides and samarium (0) [22]. This team also reported palladium-mediated allylation of the same iminoether with allylindium reagents [23].…”

Section: Reviewmentioning

confidence: 96%

Recent advancements in the homoallylamine chemistry

Puentes

Kouznetsov

2002

Journal of Heterocyclic Chem

153

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“…Consistent with this hepatobiliary excretion, the plasma exposure and pharmacokinetics of lanthanum are similar in healthy individuals and patients undergoing dialysis (Damment and Pennick 2008). Recently, the utilizations of lanthanide metal salts and organolanthanoid compounds as a reagent or catalyst in organic synthesis have steadily increased Yanada et al 2001). In contrast, there are only a few reports on the direct use of lanthanide metals except for cerium, samarium, and ytterbium metals for organic reactions (Yanada et al 2001;Bian, Yu, et al 2006).…”

Section: Please Scroll Down For Articlementioning

confidence: 80%

“…Recently, the utilizations of lanthanide metal salts and organolanthanoid compounds as a reagent or catalyst in organic synthesis have steadily increased Yanada et al 2001). In contrast, there are only a few reports on the direct use of lanthanide metals except for cerium, samarium, and ytterbium metals for organic reactions (Yanada et al 2001;Bian, Yu, et al 2006). Among the lanthanide metals, we have been interested in the use of lanthanum metal which shows higher oxidation-reduction potential, higher bond energy with oxygen, and larger atomic radius than those of other lanthanide metals (Bian, Yu, et al 2006;Bian, Zhang, et al 2006).…”

Section: Please Scroll Down For Articlementioning

confidence: 99%

High Sensitive Sensor Based on Carbon Nanotube Electrode for Determination of Lanthanum in the Presence of Calcon Carboxylic Acid

et al. 2013

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In this paper we have investigated the electrochemical activity of lanthanum chloride (La (III)) in the presence of calcon carboxylic acid (CCA) using a multi-walled carbon nano tube/carbon paste electrode (CNT/CPE). The peak current increases linearly with increasing of the La (III) concentration. For this purpose, a few electrochemical methods such as cyclic, differential pulse voltammetry, linear sweep and hydrodynamic voltammetry, and chronoamperometry were used. The results show that calcon carboxylic acid as a ligand was useful for determination of La (III) and was able to improve its sensitivity. Cyclic voltammetry was used for study of reduction reaction of La (III) at the surface of modified electrode. The electrochemical parameters for La (III) at the surface of CNT/CPE, such as diffusion coefficient (D/ cm 2 s À1 ¼ 5.26 Â 10 À6 ), the electron transfer coefficient, (a ¼ 0. 43), and the reduction rate constant, (k/ M s À1 ¼ 2.33 (AE0.015) Â 10 2 ), were determined using voltammetry methods, which with the detection limit of La (III) by differential pulse voltammetry was found to be 1.3 nM. The combination of CCA with CNT as mediators in carbon paste electrode showed that this electrode is capable, sensitive, and simple to quantify La (III) in real samples with an average recovery of 97.64%.

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Aluminum-Controlled Reactivity and Diastereoselectivity toward Radical Reactions of Optically Active Aldimines with Metallic Samarium

Abstract: The intermolecular pinacol-type coupling reaction and allylation reaction of optically active imines bearing a beta-hydroxy group were performed stereoselectively with metallic samarium after treatment of the imines with trimethylaluminum.

Cited by 34 publications

References 25 publications

Stereoselective Allylation Reactions of Imines and Related Compounds

Stereoselective Allylation Reactions of Imines and Related Compounds

Recent advancements in the homoallylamine chemistry

High Sensitive Sensor Based on Carbon Nanotube Electrode for Determination of Lanthanum in the Presence of Calcon Carboxylic Acid

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