Monomeric organoaluminium complexes RAl(OR*)2 and R2AlOR* with an optically active amino alkoxide ligand

Gelbrich, Thomas; Hecht, Elmar; Thiele, K.‐H.; Sieler, J.

doi:10.1016/s0022-328x(99)00516-1

Cited by 18 publications

(5 citation statements)

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“…During the course of our investigations on the chemistry of metal complexes supported by carboxylates and aminoalkoxides, we attempted to develop a new synthetic method leading to a novel chiral mononuclear manganese(III) complex. For this purpose, we utilized a simple amino alcohol as a proligand, that is, ( S )‐α,α‐diphenyl‐2‐pyrrolidinylmethanol (dppm‐H), which has been widely used in asymmetric organocatalysis (e.g., owing to large steric hindrance, dppm‐H has the tendency to stabilize mononuclear entities). A promising one‐pot, three‐step procedure involving a zinc aminoalkoxide intermediate followed by the addition of an Mn II carboxylate afforded the first mononuclear chiral (acetato)bis(aminoalkoxido)Mn III complex.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structure, and Magnetic Properties of a Mononuclear Chiral (Acetato)bis(aminoalkoxido)manganese(III) Complex

et al. 2017

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Section: Introductionmentioning

confidence: 99%

Synthesis, Structure, and Magnetic Properties of a Mononuclear Chiral (Acetato)bis(aminoalkoxido)manganese(III) Complex

et al. 2017

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“…In Sieler's work, 1 was obtained from the reaction of ( t Bu-Cp)Et 2 Al with 2 equiv of amino alcohol. 48 In our modified procedures, 1 and 2 can be readily prepared from the commercially available alkyl alanes and prolinol ligand to obtain the penta-coordinate complexes in one step with high yield (Scheme 1). The crystal structure of 2 (Figure S45) shows a similar C 2 -symmetric structure with the reported structural data of 1.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…In 2000, Sieler and co-workers reported a series of chiral aluminum complexes with one or two (S)-(−)-α,αdiphenyl-2-pyrrolidinyl-methanol ligands at the aluminum center. 48 However, the related cationic species and their catalytic applications remain unexplored. We noticed that the complexes bearing two prolinol ligands adopt a C 2 -symmetric geometry with a penta-coordinate aluminum atom.…”

Section: ■ Introductionmentioning

confidence: 99%

“…In light of the success of the CBS catalyst and its related compounds, the prolinol substituted aluminum complexes had been prepared. In 2000, Sieler and co-workers reported a series of chiral aluminum complexes with one or two ( S )-(−)-α,α-diphenyl-2-pyrrolidinyl-methanol ligands at the aluminum center . However, the related cationic species and their catalytic applications remain unexplored.…”

Section: Introductionmentioning

confidence: 99%

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Chiral Tetra-coordinate Aluminum Cation in Catalysis

et al. 2021

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Although the application of cationic aluminum complexes in catalysis has been extensively investigated, the incorporation of an aluminum cation into a chiral environment is less explored. In this study, a C 2 -symmetric chiral tetra-coordinate aluminum cation [3] + bearing two chiral amino alcohol-derived ligands was prepared from commercially available starting materials in two steps. The high Lewis acidity of [3] + exceeding that of B(C 6 F 5 ) 3 was verified by a competition binding experiment. Preliminary catalytic activity studies of [3] + revealed that the tetracoordinate aluminum cation is effective in accomplishing high conversion in all cases. However, the presence of a labile N−Al bond diminishes the enantioselectivity of the activation process.

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“…Dimethylaluminium-und -galliumalkoxide mit zusa È tzlichen Donoratomen in den Alkoxidresten sind in der Mehrzahl dimer aufgebaut und enthalten stabile M 2 O 2 -Ringe [3±8]. Ausnahmen sind das Dimethylaluminium-(2 S,3 R)-(+)-4-(dimethylamino)-1,2-diphenyl-3-methyl-2-butoxid [3], Di-t-butylaluminium-(S)-a,a-diphenyl-2-pyrrolidinyl-methoxid [9] und das Dimethylgallium-(S)-a,a-diphenyl-2-pyrrolidinyl-methoxid [8] La È ût man Trimethylgallium im Molverha È ltnis 1 : 1 auf o-Methoxyphenylmethylamin einwirken, so erha Èlt man das entsprechende Trimethylgallium-Amin-Addukt 5, welches in siedenden n-Pentan noch nicht zum Amid unter Methanentwicklung abreagiert. 5 bildet farblose, stark luft-und feuchtigkeitsempfindliche Kristalle, die sich gut in aliphatischen und aromatischen Kohlenwasserstoffen lo È sen.…”

Section: Introductionunclassified

Darstellung, Eigenschaften und Molekülstrukturen von Dimethylmetallalkoxiden und -amiden des Aluminiums und Galliums

Hecht

2000

Z. anorg. allg. Chem.

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Professor Egon Fangha Ènel zum 65. Geburtstag gewidmet Inhaltsu È bersicht. Dimethylaluminium-(1) und Dimethylgallium-o-methoxyphenyl-1-ethoxid (2) wurden durch Umsetzung von Me 3 Al bzw. Me 3 Ga mit o-Methoxyphenyl-1-ethanol in n-Pentan erhalten, wogegen Dimethylaluminium-(3) und Dimethylgallium-o-methoxyphenyl-2-ethylamid (4) mittels Reaktion von Me 2 AlCl bzw. Me 2 GaCl mit Lithiumo-methoxyphenyl-2-ethylamid dargestellt wurden. Trimethylgallium-o-methoxyphenylmethylamin-Addukt (5) bildet sich bei der Umsetzung von Me 3 Ga mit dem entsprechenden Amin. Die Verbindungen wurden durch 1 H-, 13 C-, 27 Al-NMR-Spektroskopie sowie 2 und 5 durch Kristallstrukturanalyse charakterisiert. 1±4 liegen als sauerstoff-bzw. stickstoffverbru È ckte dimere Moleku È le vor. Die Bindungsla È ngen im zentralen Ga 2 O 2 -Ring in 2 entsprechen denen anderer a È hnlich aufgebauter Verbindungen.Abstract. Dimethylaluminium-(1) and Dimethylgallium-omethoxyphenyl-1-ethoxide (2) were obtained by reaction of Me 3 Al and Me 3 Ga respectively with o-Methoxyphenyl-1ethanol in n-pentane. Dimethylaluminium-(3) and dimethylgallium-o-methoxyphenyl-2-ethylamide (4) were prepared by treatment of Me 2 AlCl and Me 2 GaCl respectively with Lithium-o-methoxyphenyl-2-ethylamide. Trimethylgallium-omethoxyphenylmethylamine-Adduct (5) was isolated using reaction of Me 3 Ga with the corresponding amine. The com-pounds were characterised by 1 H-, 13 C-, and 27 Al n.m.r. spectroscopy. The molecular structures of 2 and 5 were determined by X-ray diffraction. Compounds 1±4 form brigded dimeric molecules. The bond distances of the central Ga 2 O 2 ring in 2 correspond to those of compounds of similar structure.

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Monomeric organoaluminium complexes RAl(OR)2 and R2AlOR with an optically active amino alkoxide ligand

Cited by 18 publications

References 28 publications

Synthesis, Structure, and Magnetic Properties of a Mononuclear Chiral (Acetato)bis(aminoalkoxido)manganese(III) Complex

Synthesis, Structure, and Magnetic Properties of a Mononuclear Chiral (Acetato)bis(aminoalkoxido)manganese(III) Complex

Chiral Tetra-coordinate Aluminum Cation in Catalysis

Darstellung, Eigenschaften und Molekülstrukturen von Dimethylmetallalkoxiden und -amiden des Aluminiums und Galliums

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