Advances in catalytic metal-free reductions: from bio-inspired concepts to applications in the organocatalytic synthesis of pharmaceuticals and natural products

Rueping, Magnus; Dufour, Jeremy; Schoepke, Fenja R.

doi:10.1039/c1gc15027h

Cited by 279 publications

(85 citation statements)

References 233 publications

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“…Several heterocyle-based reduction reagents have been developed for this transformation in the past years [31–35]. They usually served as mild hydrogen donors, but the use of them also made the purification difficult at the same time.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of chiral N-phosphinyl α-imino esters and their application in asymmetric synthesis of α-amino esters by reduction

Xiong¹,

Mei²,

Wu³

et al. 2014

Beilstein J. Org. Chem.

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SummaryA variety of chiral N-phosphinyl α-imino esters have been synthesized for the first time from ketoesters and phosphinylamide, which were then reduced by L-selectride to give the corresponding N-phosphinyl-protected α-amino esters. The reduction proceeded very well with excellent chemical yields (88–98%) as well as high diastereoselectivities (96:4 to 99:1). Some of these products could be obtained without column chromatography and recrystallization. The chiral phosphinyl auxiliary could be easily cleaved under acidic conditions.

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Section: Introductionmentioning

confidence: 99%

Synthesis of chiral N-phosphinyl α-imino esters and their application in asymmetric synthesis of α-amino esters by reduction

Xiong¹,

Mei²,

Wu³

et al. 2014

Beilstein J. Org. Chem.

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“…45 Using cysteine-derived catalysts, only moderate, nonreproducible selectivities were reported. 46 , and benzene (3.5 mL) were added to a screw-capped vial and the mixture was exposed to an argon atmosphere. The resulting yellow solution was allowed to stir at 60 C for 3 days.…”

Section: Imine Reduction Using Hantzsch Estersmentioning

confidence: 99%

Organocatalytic Reduction in Stereoselective Synthesis

Kortmann

Minnaard

2013

Stereoselective Synthesis of Drugs and Natural Products

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The synthesis of chiral, enantiopure molecules plays an important role in modern chemistry, as stereocenters are omnipresent in natural products and pharmaceuticals. Therefore, is it important to have versatile and reliable methods to introduce stereocenters during the synthesis. An upcoming, powerful way to construct stereocenters is asymmetric organocatalytic reduction. A given prochiral double bond is selectively reduced to give one of the two enantiomers or diastereomers in excess. As substrates, the functional groups containing CN, CO, or CC double bonds come into consideration. These can appear both in linear molecules (e.g., ketones) and in heteroaromatics like pyridine. Catalysis takes place by activation of either the substrate or the reducing agent, thereby also transferring the chiral information. Hydrazine, silanes, and Hantzsch esters are herein the most frequently used reducing agents.

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“…9 Also, they can be used synthetically as reducing agents. 10,11 Heretofore, several approaches for the synthesis of 1,4-DHPs have been reported including the conventional Hantzsch condensation. The Hantzsch synthesis of 1,4-dihydropyridines is one-pot condensation of aldehydes with ethyl acetoacetate and ammonia in the presence of different catalysts and solvents.…”

Section: Introductionmentioning

confidence: 99%

A Simple and Efficient One‐pot Synthesis of 1,4‐dihydropyridines Using Nano‐WO₃‐ supported Sulfonic Acid as an Heterogeneous Catalyst under Solvent‐free Conditions

Bitaraf

Amoozadeh

Otokesh

2016

J Chinese Chemical Soc

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Nano-tungsten trioxide-supported sulfonic acid (n-WSA) was found to be an effective heterogeneous catalyst for the one-pot reaction of aromatic aldehydes, b-dicarbonyl compounds and ammonium acetate to afford 1,4-dihydropyridine derivatives in good to excellent yields. The other main advantages of the present method are short reaction times, simple workup, ease in purification and environmentally benign methodology. The reaction conditions were optimized employing Response Surface Method technique (Central Composite Design (CCD)) which is economically considerable because of the minimum number of experiments required to evaluate the effects of multiple parameters on the response.

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Advances in catalytic metal-free reductions: from bio-inspired concepts to applications in the organocatalytic synthesis of pharmaceuticals and natural products

Cited by 279 publications

References 233 publications

Synthesis of chiral N-phosphinyl α-imino esters and their application in asymmetric synthesis of α-amino esters by reduction

Synthesis of chiral N-phosphinyl α-imino esters and their application in asymmetric synthesis of α-amino esters by reduction

Organocatalytic Reduction in Stereoselective Synthesis

A Simple and Efficient One‐pot Synthesis of 1,4‐dihydropyridines Using Nano‐WO₃‐ supported Sulfonic Acid as an Heterogeneous Catalyst under Solvent‐free Conditions

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Advances in catalytic metal-free reductions: from bio-inspired concepts to applications in the organocatalytic synthesis of pharmaceuticals and natural products

Cited by 279 publications

References 233 publications

Synthesis of chiral N-phosphinyl α-imino esters and their application in asymmetric synthesis of α-amino esters by reduction

Synthesis of chiral N-phosphinyl α-imino esters and their application in asymmetric synthesis of α-amino esters by reduction

Organocatalytic Reduction in Stereoselective Synthesis

A Simple and Efficient One‐pot Synthesis of 1,4‐dihydropyridines Using Nano‐WO3‐ supported Sulfonic Acid as an Heterogeneous Catalyst under Solvent‐free Conditions

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Product

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A Simple and Efficient One‐pot Synthesis of 1,4‐dihydropyridines Using Nano‐WO₃‐ supported Sulfonic Acid as an Heterogeneous Catalyst under Solvent‐free Conditions