Enantioselective Strecker Reactions Between Aldimines and Trimethylsilyl Cyanide Promoted by Chiral N,N′‐Dioxides.

Jiao, Zhigang; Feng, Xiaoming; Liu, Bo; Chen, Fuxue; Zhang, Guolin; Jiang, Yaozhong

doi:10.1002/chin.200405072

Cited by 2 publications

(2 citation statements)

References 6 publications

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“…The compounds appear to be configurationally stable. Resolved 1,1′-biisoquinoline N,N’ -dioxides have found some applications as enantioselective organic catalysts [ 49 , 50 , 97 , 98 , 99 , 100 , 101 , 102 , 103 , 104 , 105 , 106 , 107 ]. The complex (1,1′-biisoquinoline N,N’ -dioxide)dichloridopalladium is an effective catalyst for Suzuki cross-couplings and hydroxyarylation reactions [ 96 ].…”

Section: Synthesis Of 11′-biisoquinolinesmentioning

confidence: 99%

1,1′-Biisoquinolines—Neglected Ligands in the Heterocyclic Diimine Family That Provoke Stereochemical Reflections

2021

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1,1′-Biisoquinolines are a class of bidentate nitrogen donor ligands in the heterocyclic diimine family. This review briefly discusses their properties and the key synthetic pathways available and then concentrates upon their coordination behaviour. The ligands are of interest as they exhibit the phenomenon of atropisomerism (hindered rotation about the C1–C1′ bond). A notation for depicting the stereochemistry in coordination compounds containing multiple stereogenic centers is developed. The consequences of the chirality within the ligand on the coordination behaviour is discussed in detail.

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Section: Synthesis Of 11′-biisoquinolinesmentioning

confidence: 99%

1,1′-Biisoquinolines—Neglected Ligands in the Heterocyclic Diimine Family That Provoke Stereochemical Reflections

2021

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“…The resultant intermediate species of pentacoordinated silicate was proved elsewhere by solid state 29 Si MAS NMR spectra. 25,37 Thereafter, the activated imine by Ga 3+ was attracted by the highly reactive cyanide ion to form an N-TMS intermediate. It was subsequently hydrolyzed to the Strecker product due to the cleavage of the rather labile NSi bond by a trace amount of moisture present in the solvent, which is important to accelerate the transformation of the substrate, as observed earlier by Feng et al 38 3.4.…”

Section: Strecker Reactionmentioning

confidence: 99%

Strong Lewis Base Ga₄B₂O₉: Ga–O Connectivity Enhanced Basicity and Its Applications in the Strecker Reaction and Catalytic Conversion of n-Propanol

Hu¹,

Wang²,

Yue³

et al. 2018

ACS Appl. Mater. Interfaces

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Heterogeneous solid base catalysis is valuable and promising in chemical industry, however it is insufficiently developed compared to solid acid catalysis due to the lack of satisfied solid base catalysts. To gain the strong basicity, the previous strategy was to basify oxides with alkaline metals to create surficial vacancies or defects, which suffers from the instability under catalytic conditions. Monocomponent basic oxides like MgO are literally stable but deficient in electron-withdrawing ability. Here we prove that a special connectivity of atoms could enhance the Lewis basicity of oxygen in monocomponent solids exemplified by GaBO. The structure-induced basicity is from the μ-O linked exclusively to five-coordinated Ga. GaBO behaved as a durable catalyst with a high yield of 81% in the base-catalyzed synthesis of α-aminonitriles by Strecker reaction. In addition, several monocomponent solid bases were evaluated in the Strecker reaction, and GaBO has the largest amount of strong base centers (23.1 μmol/g) and the highest catalytic efficiency. GaBO is also applicable in high-temperature solid-gas catalysis, for example, GaBO catalyzed efficiently the dehydrogenation of n-propanol, resulting in a high selectivity to propanal (79%). In contrast, the comparison gallium borate, Ga-PKU-1, which is a Brönsted acid, preferred to catalyze the dehydration process to obtain propylene with a selectivity of 94%.

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Enantioselective Strecker Reactions Between Aldimines and Trimethylsilyl Cyanide Promoted by Chiral N,N′‐Dioxides.

Abstract: For Abstract see ChemInform Abstract in Full Text.

Cited by 2 publications

References 6 publications

1,1′-Biisoquinolines—Neglected Ligands in the Heterocyclic Diimine Family That Provoke Stereochemical Reflections

1,1′-Biisoquinolines—Neglected Ligands in the Heterocyclic Diimine Family That Provoke Stereochemical Reflections

Strong Lewis Base Ga₄B₂O₉: Ga–O Connectivity Enhanced Basicity and Its Applications in the Strecker Reaction and Catalytic Conversion of n-Propanol

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Enantioselective Strecker Reactions Between Aldimines and Trimethylsilyl Cyanide Promoted by Chiral N,N′‐Dioxides.

Abstract: For Abstract see ChemInform Abstract in Full Text.

Cited by 2 publications

References 6 publications

1,1′-Biisoquinolines—Neglected Ligands in the Heterocyclic Diimine Family That Provoke Stereochemical Reflections

1,1′-Biisoquinolines—Neglected Ligands in the Heterocyclic Diimine Family That Provoke Stereochemical Reflections

Strong Lewis Base Ga4B2O9: Ga–O Connectivity Enhanced Basicity and Its Applications in the Strecker Reaction and Catalytic Conversion of n-Propanol

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Strong Lewis Base Ga₄B₂O₉: Ga–O Connectivity Enhanced Basicity and Its Applications in the Strecker Reaction and Catalytic Conversion of n-Propanol