Ozonolysis Applications in Drug Synthesis

Ornum, Scott G. Van; Champeau, Robin M.; Pariza, R. J.

doi:10.1021/cr040682z

Cited by 245 publications

(162 citation statements)

References 51 publications

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“…Our attention was therefore turned to the less reactive triacetoxyborohydride, which has been investigated little in ozonolysis/amination sequences. 12, 13 We now report that NaBH(OAc) 3 allows rapid and efficient reduction of ozonolysis-derived hydroperoxyacetals to aldehydes, enabling a mild and convenient one-pot synthesis of amines from alkenes based upon ozonolysis and reductive amination.…”

mentioning

confidence: 96%

“…2 The carbonyl precursors are often prepared from alkenes through ozonolysis followed by reduction of the ozonide or peroxide intermediates. 3,4 In the course of investigations into new transformations based upon fragmentation of ozonolysis intermediates, 5 we became interested in the development of a mild method for a one-pot conversion of alkenes to amines. Reductive amination is frequently achieved through the reaction of carbonyls and amines in the presence of deactivated boron hydrides, 2b, 6, 7 and NaCNBH 3 -promoted reductive amination has been applied in tandem with ozonolysis.…”

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confidence: 99%

“…It was found that NaBH(OAc) 3 offered high selectivity for aldehyde formation in several different solvent systems (CH 2 Cl 2 , DCE, THF) and under several sets of conditions. Performing the reduction with one equivalent of NaBH(OAc) 3 proved optimal; and excess of reducing reagent (1.5-3 equiv) led to slow overreduction of the aldehyde. In contrast, the use of the more reactive NaCNBH 3 in stoichiometric amounts cleanly generated alcohol, while a mixture of alcohol and starting material was observed even with only 0.33 equivalent of reagent.…”

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confidence: 99%

“…Reduction with NaBH(OAc) 3 was next applied to a wider group of hydroperoxyacetals (Table 2). Hydroperoxyacetals reacted faster (2 h) than hydroperoxyketals (5-8 h).…”

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confidence: 99%

“…Reductive amination was easily conducted through reduction of the hydroperoxyacetal with NaBH(OAc) 3 (1 equiv), followed by addition of amine and additional hydride (Scheme 1). The reactions were found to give good yields of monoalkylated amines.…”

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A Mild One-Pot Conversion of Alkenes into Amines through Tandem Ozonolysis and Reductive Amination

Kyasa¹,

Fisher²,

Dussault³

2011

Synthesis

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confidence: 96%

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confidence: 99%

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confidence: 99%

“…Reduction with NaBH(OAc) 3 was next applied to a wider group of hydroperoxyacetals (Table 2). Hydroperoxyacetals reacted faster (2 h) than hydroperoxyketals (5-8 h).…”

mentioning

confidence: 99%

mentioning

confidence: 99%

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A Mild One-Pot Conversion of Alkenes into Amines through Tandem Ozonolysis and Reductive Amination

Kyasa¹,

Fisher²,

Dussault³

2011

Synthesis

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Visible‐light‐mediated Oxidative Debenzylation of 3‐ O ‐Benzyl‐1,2:5,6‐di‐ O ‐isopropylidene‐α‐D‐glucofuranose

Madani,

Sletten,

Cavedon

et al. 2024

Organic Syntheses

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This chapter presents the procedure for the visible‐light‐mediated oxidative debenzylation of 3‐O‐benzyl‐1,2:5,6‐ di‐O‐isopropylidene‐α‐d‐glucofuranose . Benzyl ethers are important protective groups in the synthesis of carbohydrates due to their excellent stability over a wide range of conditions. However, benzyl ether cleavage requires harsh reduction/oxidation processes, such as catalytic hydrogenolysis, Birch reduction, or oxidation with ozone or BCl, that are hazardous, and poorly functional group tolerant. The photooxidative debenzylation strategy overcomes current limitations of benzyl ethers as protecting groups that arise from the harsh conditions necessary for their cleavage. The methodology enables the use of benzyl ethers as orthogonal protective group that is installed and removed throughout the synthesis of complex molecules and clears the path to the development of new synthetic routes in total synthesis.

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Oxidation

Teles

Hermans

Franz³

et al. 2015

Ullmann's Encyclopedia of Industrial Chemistry

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The article contains sections titled: 1. Introduction 2. Overview of industrial oxidation processes 2.1. Inorganic chemicals 2.1.1. Sulfur derivatives 2.1.2. Carbon derivatives 2.1.3. Nitrogen derivatives 2.1.4. Chlorine derivatives 2.2. Organic chemicals 2.2.1. Olefins and alkynes 2.2.2. Epoxides 2.2.3. Hydroperoxides 2.2.4. Alcohols 2.2.5. Aldehydes 2.2.6. Ketones 2.2.7. Phenols and derivatives 2.2.8. Carboxylic acids, saturated 2.2.9. Carboxylic acids and anhydrides, unsaturated 2.2.10. Carboxylic acids and anhydrides, aromatic 2.2.11. Esters, lactones and carbonates 2.2.12. Nitriles 2.2.13. Oxidized nitrogen compounds 2.2.14. Chlorinated compounds 2.2.15. Sulfur compounds 3. Thermodynamics; Stability of Hydrocarbons 4. Reaction Types 5. Homolytic Oxidation 5.1. Historical Development; Reaction Mechanism; Radical Reactivity 5.2. Kinetics of Autoxidation 5.3. Differences between Liquid‐ and Gas‐Phase Autoxidations 5.4. Homolytic Oxidation in the Liquid Phase 5.4.1. Secondary Reactions of Radicals, Peroxides, and other Intermediates 5.4.2. Metal Catalysis in Homolytic Liquid‐Phase Oxidation 5.4.3. Inhibitors of Homolytic Liquid‐Phase Oxidation 5.4.4. Special Cases of Homolytic Oxidation 5.4.5. Process Technology of Homolytic Liquid‐Phase Oxidation 5.5. Homolytic Gas‐Phase Oxidation 5.6. Gas Explosions and Safety Data 6. Heterolytic Oxidation 6.1. Heterolytic Oxidation in the Liquid Phase 6.2. Heterogeneously Catalyzed Gas‐Phase Oxidation 6.2.1. Oxidation Catalysts 6.2.2. Process Technology of Heterogeneously Catalyzed Oxidations

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Ozonolysis Applications in Drug Synthesis

Cited by 245 publications

References 51 publications

A Mild One-Pot Conversion of Alkenes into Amines through Tandem Ozonolysis and Reductive Amination

A Mild One-Pot Conversion of Alkenes into Amines through Tandem Ozonolysis and Reductive Amination

Visible‐light‐mediated Oxidative Debenzylation of 3‐ O ‐Benzyl‐1,2:5,6‐di‐ O ‐isopropylidene‐α‐D‐glucofuranose

Oxidation

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