ChemInform Abstract: Chirality Transfer in Metal-Catalyzed Intermolecular Addition Reactions Involving Allenes

ChemInform ◽  
2016 ◽  
Vol 47 (46) ◽  
Author(s):  
Jose Miguel Alonso ◽  
Maria Teresa Quiros ◽  
Maria Paz Munoz
Keyword(s):  
Addition Reactions ◽  
Chirality Transfer ◽  
Metal Catalyzed

scholarly journals Chiral Aziridine Sulfide N(sp3),S-Ligands for Metal-Catalyzed Asymmetric Reactions

Symmetry ◽  
2021 ◽  
Vol 13 (3) ◽  
pp. 502
Author(s):  
Agata J. Pacuła-Miszewska ◽  
Anna Laskowska ◽  
Anna Kmieciak ◽  
Mariola Zielińska-Błajet ◽  
Marek P. Krzemiński ◽  
...  
Keyword(s):  
Metal Binding ◽  
Electronic Effect ◽  
Asymmetric Reactions ◽  
Addition Reactions ◽  
Phenyl Sulfide ◽  
Enantiomeric Ratio ◽  
Catalyzed Reactions ◽  
Metal Catalyzed ◽  
Sulfide Group

A series of new bidentate N,S-ligands—aziridines containing a para-substituted phenyl sulfide group—was synthesized and evaluated in the Pd-catalyzed Tsuji–Trost reaction and addition of diethylzinc and phenylethynylzinc to benzaldehyde. A high enantiomeric ratio for the addition reactions (up to 94.2:5.8) was obtained using the aziridine ligand bearing a p-nitro phenyl sulfide group. Collected results reveal a specific electronic effect that, by the presence of particular electron-donating or electron-withdrawing groups in the PhS- moiety, influences the σ-donor–metal binding and the enantioselectivity of the catalyzed reactions.

Amide-Directed Reactions of Small Carbocycles

2021 ◽  
Vol 25 ◽  
Author(s):  
Pavel M. Yamanushkin ◽  
Marina Rubina ◽  
Michael Rubin
Keyword(s):  
Transition Metal ◽  
Transition Metals ◽  
Nucleophilic Addition ◽  
Addition Reactions ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

: The topic of this review is the amide-directed functionalization of strained carbocycles — specifically, unsaturated or saturated three- and four-membered rings. The following approaches are discussed: a) directed carbometallation and hydrometallation of cyclopropenes catalyzed by transition metals; b) directed metal-templated nucleophilic addition reactions; c) directed C-H functionalization, including transition metal-catalyzed C-H-activation reactions; and d) directed radical additions.

Transition-Metal-Catalyzed Synthesis of Organophosphorus Compounds Involving P–P Bond Cleavage

Synthesis ◽  
2020 ◽  
Vol 52 (19) ◽  
pp. 2795-2806 ◽  
Author(s):  
Mieko Arisawa
Keyword(s):  
Transition Metal ◽  
Organophosphorus Compounds ◽  
Bond Cleavage ◽  
Palladium Complexes ◽  
Addition Reactions ◽  
Phosphonium Salts ◽  
Substitution Reactions ◽  
Sulfonic Acids ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Organophosphorus compounds are used as drugs, pesticides, detergents, food additives, flame retardants, synthetic reagents, and catalysts, and their efficient synthesis is an important task in organic synthesis. To synthesize novel functional organophosphorus compounds, transition-metal-catalyzed methods have been developed, which were previously considered difficult because of the strong bonding that occurs between transition metals and phosphorus. Addition reactions of triphenylphosphine and sulfonic acids to unsaturated compounds in the presence of a rhodium or palladium catalyst lead to phosphonium salts, in direct contrast to the conventional synthesis involving substitution reactions of organohalogen compounds. Rhodium and palladium complexes catalyze the cleavage of P–P bonds in diphosphines and polyphosphines and can transfer organophosphorus groups to various organic compounds. Subsequent substitution and addition reactions proceed effectively, without using a base, to provide various novel organophosphorus compounds.1 Introduction2 Transition-Metal-Catalyzed Synthesis of Phosphonium Salts by Addition Reactions of Triphenylphosphine and Sulfonic Acids3 Rhodium-Catalyzed P–P Bond Cleavage and Exchange Reactions4 Transition-Metal-Catalyzed Substitution Reactions Using Diphosphines4.1 Reactions Involving Substitution of a Phosphorus Group by P–P Bond Cleavage4.2 Related Substitution Reactions of Organophosphorus Compounds4.3 Substitution Reactions of Acid Fluorides Involving P–P Bond Cleavage of Diphosphines5 Rhodium-Catalyzed P–P Bond Cleavage and Addition Reactions6 Rhodium-Catalyzed P–P Bond Cleavage and Insertion Reactions Using Polyphosphines7 Conclusions

scholarly journals Chirality transfer in metal-catalysed intermolecular addition reactions involving allenes

2016 ◽  
Vol 3 (9) ◽  
pp. 1186-1204 ◽  
Author(s):  
José Miguel Alonso ◽  
María Teresa Quirós ◽  
María Paz Muñoz
Keyword(s):  
Asymmetric Catalysis ◽  
Addition Reactions ◽  
Chirality Transfer

This review covers chirality transfer in metal-catalysed intermolecular addition reactions involving allenes, including axial-to-central chirality transfer, asymmetric catalysis and racemization.

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