Popular Synthetic Approaches To Pharmaceuticals

Ager, David J.

doi:10.1055/s-0034-1379733

Cited by 10 publications

(6 citation statements)

References 54 publications

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“…Homogeneous hydrogenation has advanced significantly over the last 40 years and is now the most practical process in contemporary science and technology. [12][13][14][15] Consequently, the topic of this review focused on asymmetric hydrogenation based on homogeneous catalysis. Knowles and Horner individually discovered homogeneous asymmetric hydrogenation for the first time in 1968 Figure 1.…”

Section: Introductionmentioning

confidence: 99%

A concise review on recent advances in catalytic asymmetric hydrogenation

et al. 2023

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Accounts on the recent (over the past 10 years) catalytic asymmetric hydrogenation reaction‐based achievements with different catalysts to generate natural products and synthetic targets such as fragrances, pharmaceutical agents, and agrochemicals are mentioned in this present concise review. Mechanistic steps, chemoselectivity with higher functional group tolerance by employing transition metal‐based chiral catalysts (Ir‐, Rh‐, Ni‐, Ru‐, Fe‐, Mn‐, Pd‐, Co‐, and Zn‐based organometallic chiral complexes), and biocatalysts and their importance on the genesis of chirality coupled with higher turnover numbers are also described.

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Section: Introductionmentioning

confidence: 99%

A concise review on recent advances in catalytic asymmetric hydrogenation

et al. 2023

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“…Catalytic asymmetric hydrogenation provides a convenient and practical method to prepare chiral alcohols, amines and alkanes from prochiral substrates. The use of hydrogen gas as the reductant (asymmetric direct hydrogenation, ADH) offers 100% atom economy and has a long track record of success in the industrial production of single enantiomer advanced pharmaceutical intermediates (API) − as recognized by the Nobel prize to Knowles and Noyori . This has inspired a huge academic research effort which continues to this day that provides leads for future successful applications.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Homogeneous Asymmetric Hydrogenation: Successes and Opportunities

2018

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This is an overview of successes in the realm of catalytic homogeneous asymmetric hydrogenation of substrates primarily of interest in the synthesis of pharmaceuticals in order to identify important problems still unsolved. First, tables are provided that list the successful reductions to over 90% enantiomeric excess of prochiral ketones to alcohols, imines to amines, and olefins to saturated carbon centers. Noted in the tables are the metal (including "green" metals Mn, Fe, and Co) or enzyme, the class of ligand, the conditions of the medium, and the scale of reduction, if over 1 kg of product, as well as the nature of the process, whether direct hydrogenation using H 2 gas (DH), transfer hydrogenation (TH), or hydrogenation with dynamic kinetic resolution (DKR). Tables of representative pharmaceutical or fine chemicals products are provided for each class of substrate. With this overview, the opportunities for further research and development become clearer.

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“…Recently, the transition-metal-catalyzed cross-couplings of (Me 3 Si) 2 MgBr·LiCl or (Me 3 Si) 2 ZnCl·MgBrCl·LiCl with aryl halides has been reported as an additional route to this reagent class . The synthetic value of reagents 6 lies in their bench stability, yet under mild activation conditions they can react as equivalents of the α-silyl carbanions 5 in Peterson olefination reactions. ,, The utility of reagents 6 for E -selective Peterson olefination from N -phenyl imines has recently been reported …”

Section: Introductionmentioning

confidence: 99%

General Ambient Temperature Benzylic Metalations Using Mixed-Metal Li/K-TMP Amide

2015

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Highly regioselective benzylic metalations in hydrocarbon solvent have been achieved at rt and 0 °C using a mixed-metal Li/K-TMP amide comprised of KOtBu, BuLi, and 2,2,6,6,-tetramethylpiperidine (TMP(H)). Mixing of KOtBu, BuLi, and TMP(H) in heptane gave a solution of the base mixture which when used in deuterium labeling experiments confirmed the requirement of the three reagent components for both reactivity and selectivity. The reaction protocol is operationally straightforward and found to be applicable to a broad range of substrates. Upon generation of the metalated products, they are reacted in heptane at ambient temperature in a variety of synthetically useful ways. Illustrated examples include generation of the benzyltrimethylsilanes and α,α-bis(trimethylsilyl)toluenes reagents, which are bench-stable surrogates of benzyl anions and α-silyl carbanions utilized for nucleophilic addition and Peterson olefination reactions. Direct C-C couplings mediated by 1,2-dibromoethane provided entries into bibenzyls and [2.2]metacyclophanes. Comparison of reaction outcomes with the same reactions carried out in THF at -78 °C showed no negative effects for conducting the reactions under these milder more user-friendly conditions.

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Popular Synthetic Approaches To Pharmaceuticals

Cited by 10 publications

References 54 publications

A concise review on recent advances in catalytic asymmetric hydrogenation

A concise review on recent advances in catalytic asymmetric hydrogenation

Catalytic Homogeneous Asymmetric Hydrogenation: Successes and Opportunities

General Ambient Temperature Benzylic Metalations Using Mixed-Metal Li/K-TMP Amide

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