Applications of Asymmetric Petasis Reaction in the Synthesis of Chiral Amines

Li, Yi; Xu, Ming‐Hua

doi:10.6023/a21080391

Cited by 3 publications

(3 citation statements)

References 82 publications

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“…Then, the phenol functional group activates the boronic acid, generating a tetrahedral boronate salt intermediate (the "ate complex"), which is capable of transferring the boron substituent to the iminium moiety, affording the Petasis adduct [10][11][12]. One of the main advantages of the Petasis MCR, even when compared to several other MCRs, is its suitability to undergo catalytic asymmetric transformations, which is of great interest for drug discovery and API synthesis [13,14]. Enantioselectivity can be induced through the use of reagents from the chiral pool or asymmetric catalysts.…”

Section: Introductionmentioning

confidence: 99%

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The Asymmetric Petasis Borono-Mannich Reaction: Insights on the Last 15 Years

Marques

Brandão

2023

Catalysts

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The Petasis borono-Mannich reaction, commonly described as the Petasis reaction, was one of the latest famous multicomponent reactions described in the literature. Currently celebrating its 30th anniversary since it was first reported by Petasis and Akritopoulou in 1993, this reaction has emerged as a powerful tool for the synthesis of biologically relevant molecules (such as substituted amines or amino acids), among others. This three-component catalyst-free reaction (the classic model), involving the coupling of an aldehyde, an amine, and a boronic acid, enables the synthesis of polysubstituted amine-containing molecules. Several accounts regarding the catalyst-free version using different carbonyl, amine, and boron-type components have been reported thus far. In contrast, the asymmetric version is still in its infancy since it was first reported in 2007. In this work, we aim to review the asymmetric versions of the Petasis reaction reported over the last 15 years, considering the chiral pool approach (asymmetric induction by one reaction component) and the use of catalysts (organocatalysts, transition-metal catalysts, and others) to access enantiomeric and diastereomeric pure amino-derivatives. Insights regarding the catalyzed Petasis reaction and consequent sustainable synthesis will be highlighted.

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Section: Introductionmentioning

confidence: 99%

“…One of the main advantages of the Petasis MCR, even when compared to several other MCRs, is its suitability to undergo catalytic asymmetric transformations, which is of great interest for drug discovery and API synthesis [13,14]. Enantioselectivity can be induced through the use of reagents from the chiral pool or asymmetric catalysts.…”

Section: Introductionmentioning

confidence: 99%

The Asymmetric Petasis Borono-Mannich Reaction: Insights on the Last 15 Years

Marques

Brandão

2023

Catalysts

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“…Efficient and convenient synthesis of chiral amine compounds is an important direction for the research of organic synthetic chemistry [1] . The Petasis reaction is one of the synthetic methods [2] . Nowadays in the chemical synthesis of chiral amine compounds, catalysis is the main direction of integrating high efficiency and green environmental protection.…”

Section: Introductionmentioning

confidence: 99%

Advances in Asymmetric N Construction of Metal and Organic Small Molecules

2022

AJMC

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Lot of natural products, pharmaceuticals and functional materials with chiral amines do many useful job, and this group also a valuable constituents of versatile building blocks and important chiral catalysts as well as chiral auxiliaries in organic synthesis. Therefore, to develop efficient methods for the synthesis of structurally diverse chiral amines and chiral amine scaffolds has great importance and huge application vaule. symmetric catalysis is the most efficient method to synthesize chiral organic molecules. Cooperatively catalyzed by transition metal and small organic molecules can be used to simultaneously or continuously activates the bonds and rebuild, it can help some reaction which can not happen with only one catalyst to move on. This article reviews some cases of chiral nitrogen formation through metal catalysis, organic small molecule catalysis and their synergistic catalysis, and briefly discusses the challenges and future development directions in this area.

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Development of Construction of Chiral C—X Bonds through Nickel Catalyzed Asymmetric Hydrogenation^★

Cai¹,

Chen²,

Zhang³

2023

Acta Chimica Sinica

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Chiral C-X (X＝N, O, P, B, F, etc.) bond fragments are present in a wide variety of natural and pharmaceutically active molecules. Transition metal-catalyzed asymmetric hydrogenation is one of the most attractive strategies for the synthesis of these chiral compounds. Among the many transition metal catalysts, earth-abundant transition metals (iron, cobalt, nickel, and copper) have been used in asymmetric hydrogenation to replace rare metals (rhodium, ruthenium, iridium and palladium) due to their abundant reserves, low toxicity, and environmental friendliness. At present, this method for the construction of chiral C-X bonds has become a prominent trend in modern organic chemistry. Among them, the development of nickel catalysts has been relatively rapid. Based on this, the article will review the latest research in the preparation of compounds with chiral C-X bonds via nickel-catalyzed asymmetric hydrogenation using hydrogen. It is divided into five sections consisting of the construction of chiral C-N, C-O, C-P, C-B and C-F bonds by nickel-catalyzed asymmetric hydrogenation.

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Applications of Asymmetric Petasis Reaction in the Synthesis of Chiral Amines

Cited by 3 publications

References 82 publications

The Asymmetric Petasis Borono-Mannich Reaction: Insights on the Last 15 Years

The Asymmetric Petasis Borono-Mannich Reaction: Insights on the Last 15 Years

Advances in Asymmetric N Construction of Metal and Organic Small Molecules

Development of Construction of Chiral C—X Bonds through Nickel Catalyzed Asymmetric Hydrogenation^★

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Applications of Asymmetric Petasis Reaction in the Synthesis of Chiral Amines

Cited by 3 publications

References 82 publications

The Asymmetric Petasis Borono-Mannich Reaction: Insights on the Last 15 Years

The Asymmetric Petasis Borono-Mannich Reaction: Insights on the Last 15 Years

Advances in Asymmetric N Construction of Metal and Organic Small Molecules

Development of Construction of Chiral C—X Bonds through Nickel Catalyzed Asymmetric Hydrogenation★

Contact Info

Product

Resources

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Development of Construction of Chiral C—X Bonds through Nickel Catalyzed Asymmetric Hydrogenation^★