Magnesium iodide promoted reactions of nitrones with cyclopropanes: a synthesis of tetrahydro-1,2-oxazines.

doi:10.1021/JO048768F

Paper

Magnesium iodide promoted reactions of nitrones with cyclopropanes: a synthesis of tetrahydro-1,2-oxazines.

Published Nov 5, 2004 · Michael D. Ganton, M. Kerr

The Journal of organic chemistry

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Abstract

Anhydrous magnesium iodide (MgI(2)) is shown to be an effective promoter of the "homo 3+2" dipolar cycloaddition of nitrones with 1,1-cyclopropane diesters. In almost all cases the products tetrahydro-1,2-oxazines are formed in excellent yields. The reactions are highly diastereoselective for a cis relationship between the substitutents at the 3- and 6-positions on the tetrahydrooxazine ring. As an alternative to using a preformed nitrone, the reaction may be performed in a 3-component sense by combining an aldehyde, an hydroxylamine, and the cyclopropane in the presence of catalytic MgI(2).

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Study Snapshot

Magnesium iodide effectively promotes the dipolar cycloaddition of nitrones to 1,1-cyclopropane diesters, leading to excellent yields of tetrahydro-1,2-oxazines with high diastereoselectivity.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Magnesium iodide promoted reactions of nitrones with cyclopropanes: a synthesis of tetrahydro-1,2-oxazines.

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References

Citations

Reductive Coupling of Nitroarenes and HCHO for General Synthesis of Functional Ethane-1,2-diamines by a Cobalt Single-Atom Catalyst.

A bifunctional cobalt single-atom catalyst (CoSA-N/NC) effectively synthesizes functional ethane-1,2-diamines by selectively reductive coupling nitroarenes and formaldehyde, offering high reusability and efficiency.

Facile access to [1,2]-oxazine derivatives via annulations of aminoxy-tethered 1,7-enynes.

This study developed a diastereoselective approach for the construction of functionalized cyclopenta[d][1,2]oxazines from readily accessible propargylic alcohols, enabling the access to cyclopentenone-based amino alcohols.

Total Synthesis of (±)-Phyllantidine: Development and Mechanistic Evaluation of a Novel Ring Expansion for Installation of Embedded Nitrogen-Oxygen Bonds.

This study presents a novel synthetic strategy for ()-phyllantidine, a member of the securinega family, using ring expansion to facilitate the installation of embedded nitrogen-oxygen bonds.

Donor–Acceptor Cyclopropanes as an Expedient Building Block Towards the Construction of Nitrogen‐Containing Molecules: An Update

Donor-acceptor cyclopropanes (DACs) are effective building blocks for the synthesis of nitrogen-containing molecules of pharmaceutical and industrial importance.

One-Pot Au[III]-/Lewis Acid Catalyzed Cycloisomerization of Nitroalkynes and [3 + 3]Cycloaddition with Donor-Acceptor Cyclopropanes.

This one-pot protocol enables the synthesis of a tricyclic pseudoindoxyl scaffold from 2-nitroalkynylbenzenes by utilizing Au(III)-catalyzed nitroalkyne cycloisomerization and Lewis acid-mediated [3 + 3]

Recent Advances in the Chemistry of Doubly Activated Cyclopropanes: Synthesis and Reactivity

Doubly activated cyclopropanes are useful synthons for the synthesis of natural products and functionalized molecules due to their regioselective ring opening and 1,3 dipolar cycloaddition reactions.

Synthesis and Transformations of Nitrones for Organic Synthesis.

Nitrones are key intermediates for the synthesis of biologically important nitrogen compounds, and their synthesis and transformations provide strategies for their construction.