Alkene ozonolysis

Fisher, Thomas J.; Dussault, Patrick H.

doi:10.1016/j.tet.2017.03.039

Cited by 120 publications

(104 citation statements)

References 310 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…11 As a consequence, a glyoxylate equivalent was required and found in dimethyl maleate. The oxathiolane core was synthesized in 87% yield by cleaving dimethyl maleate with ozone 12 and reacting the aldehyde generated in situ with dithianediol. It can be used directly or purified through a brinebased extraction procedure.…”

Section: ■ Completing An Economical 3tc Synthesismentioning

confidence: 99%

An Economical Route to Lamivudine Featuring a Novel Strategy for Stereospecific Assembly

Snead

McQuade

Ahmad

et al. 2020

Org. Process Res. Dev.

View full text Add to dashboard Cite

An economical synthesis of lamivudine was developed by employing a new method to establish the stereochemistry about the heterocyclic oxathiolane ring. Toward this end, an inexpensive and readily accessible lactic acid derivative served the dual purpose of activating the carbohydrate's anomeric center for N-glycosylation and transferring stereochemical information to the substrate simultaneously. Both enantiomers of the lactic acid derivative are available, and either β-enantiomer in this challenging class of 2′-deoxynucleoside active pharmaceutical ingredients can be formed.

show abstract

Section: ■ Completing An Economical 3tc Synthesismentioning

confidence: 99%

An Economical Route to Lamivudine Featuring a Novel Strategy for Stereospecific Assembly

Snead

McQuade

Ahmad

et al. 2020

Org. Process Res. Dev.

View full text Add to dashboard Cite

show abstract

“…The reaction mixture was stirred for 5 or 24 h at 20-25°C. Later, saturated aqueous NH 4 Cl (10 mL) was added, the mixture was extracted with CH 2 Cl 2 (3 × 15 mL), dried over Na 2 SO 4 , filtered and concentrated under reduced pressure using a rotary evaporator (15)(16)(17)(18)(19)(20), (bath temperature, ca. 20-25°C).…”

Section: Entries 1-11mentioning

confidence: 99%

“…The main approaches to oxidation of double bond by oxygen-containing oxidizers [16] are [2 + 2] cycloaddition of singlet oxygen resulted in dioxetanes, [17] ozonolysis providing ozonides [18] and processes including oxidation by oxygen-based systems, [19] oxaziridines, [20] inorganic oxygen-containing oxidizers, [21] peracids, [22] dioxiranes, [23] and systems based on ROOH [24] (Scheme 1). In this study we disclosed power of oxidative [5 + 2] cycloaddition of malonyl peroxide and double bond [6a,7] as an alternative strategy to double bond oxidation (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

C−O coupling of Malonyl Peroxides with Enol Ethers via [5+2] Cycloaddition: Non‐Rubottom Oxidation

et al. 2019

View full text Add to dashboard Cite

Malonyl peroxides act both as oxidants and reagents for C−O coupling in reactions with methyl and silyl enol ethers. In the proposed conditions, the oxidative C−O coupling of malonyl peroxides with enol ethers selectively proceeds, bypassing the traditional Rubottom hydroxylation of enol ethers by peroxides. It was observed that the oxidative [5+2] cycloaddition of malonyl peroxides and enol ethers is the key stage of the discovered process. Oxidative C−O coupling of silyl enol ethers leads to the formation of α‐acyloxyketones with a free carboxylic acid group. A specially developed preparative one‐pot procedure transforms ketones via silyl enol ethers formation and the following coupling into α‐acyloxyketones with yields 35–88%. The acid‐catalyzed coupling with methyl enol ethers gives remarkable products while retaining the easily oxidizable enol fragment. Furthermore, these molecules contain a free carboxylic acid group, thus these nontrivial products contain two usually incompatible acid and enol ether groups.

show abstract

“…There are two main methodologies in the literature for oxidative ring opening: either through ozonolysis of alkenes or cleavage of vicinal diols. [36][37][38][39][40][41] Both are useful methods to prepare synthetically valuable dialdehydes or diketones. [39] The Upjohn method is a two-step procedure for the cleavage of the CÀ C double bond.…”

Section: Synthesis Of Saturated N-heterocycles From Dialdehyde Compoundsmentioning

confidence: 99%

Stereocontrolled Synthesis of Functionalized Azaheterocycles from Carbocycles through Oxidative Ring Opening/Reductive Ring Closing Protocols

Kiss

Ouchakour

Ábrahámi

et al. 2019

The Chemical Record

View full text Add to dashboard Cite

Fluorine‐containing organic scaffolds are of significant interest in medicinal chemistry. The incorporation of fluorine into biomolecules can lead to remarkable changes in their physical, chemical, and biological properties. There are already many drugs on the market, which contain at least one fluorine atom. Saturated functionalized azaheterocycles as bioactive substances have gained increasing attention in pharmaceutical chemistry. Due to the high biorelevance of organofluorine molecules and the importance of N‐heterocyclic compounds, selective stereocontrolled procedures to the access of new fluorine‐containing saturated N‐heterocycles are considered to be a hot research topic. This account summarizes the synthesis of functionalized and fluorine‐containing saturated azaheterocycles starting from functionalized cycloalkenes and based on oxidative ring cleavage of diol intermediates followed by ring expansion with reductive amination.

show abstract

Alkene ozonolysis

Cited by 120 publications

References 310 publications

An Economical Route to Lamivudine Featuring a Novel Strategy for Stereospecific Assembly

An Economical Route to Lamivudine Featuring a Novel Strategy for Stereospecific Assembly

C−O coupling of Malonyl Peroxides with Enol Ethers via [5+2] Cycloaddition: Non‐Rubottom Oxidation

Stereocontrolled Synthesis of Functionalized Azaheterocycles from Carbocycles through Oxidative Ring Opening/Reductive Ring Closing Protocols

Contact Info

Product

Resources

About