Domino Reactions of Bis-Diazo Compounds: Rhodium(II) Acetate Catalyzed Diastereoselective Synthesis of Epoxy- and Epithio-Bridged Heterocycle-Fused Quinolizinone Analogues

doi:10.1055/s-0035-1560441

Paper

Domino Reactions of Bis-Diazo Compounds: Rhodium(II) Acetate Catalyzed Diastereoselective Synthesis of Epoxy- and Epithio-Bridged Heterocycle-Fused Quinolizinone Analogues

Published Apr 13, 2016 · S. Muthusamy, C. Gangadurai

Synthesis

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7

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Abstract

Abstract Rhodium(II) acetate catalyzed domino reactions of bis-diazo compounds afford epoxy- and epithio-bridged heterocycle-fused quinolizinone systems in a stereoselective manner. The presence of an acceptor diazo functionality leads to a selective intermolecular X–H insertion reaction in a chemoselective manner, and the acceptor/acceptor diazo functionality subsequently participates in the formation of isomünchnone/thioisomünchnone 1,3-dipoles followed by intramolecular cycloaddition in a diastereoselective manner. This domino reaction is capable of constructing epoxy- and epithio-bridged heterocycle-fused quinolizinone ring systems with four stereogenic centers. The Brønsted acid induced reactions of oxa-bridged tricyclic compounds furnish ring-opened alcohol products in a regioselective manner.

Study Snapshot

Rhodium(II) acetate catalyzed domino reactions of bis-diazo compounds lead to the stereoselective synthesis of epoxy- and epithio-bridged heterocycle-fused quinolizinone analogues.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

Domino Reactions of Bis-Diazo Compounds: Rhodium(II) Acetate Catalyzed Diastereoselective Synthesis of Epoxy- and Epithio-Bridged Heterocycle-Fused Quinolizinone Analogues

References

Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides

Modern catalytic methods for organic synthesis with diazo compounds enable the synthesis of ylides, aromatic compounds, and various metal carbene transformations.

Citations

ADVANCES AND PROSPECTS IN RHODIUM CATALYZED DOMINO REACTIONS

Rhodium-catalyzed domino reactions have made significant progress due to their high reaction efficiency and regio-, stereo-, and enantioselectivity in organic synthesis.

Preparation and Synthetic Applications of Five-to-Seven-Membered Cyclic α-Diazo Monocarbonyl Compounds

Cyclic α-diazo monocarbonyl compounds exhibit unique reactivity, with this review summarizing their synthesis and applications in three major classes: α-diazo ketones, α-diazo lactones, and α-diazo lactams.

“On water” cascade synthesis of benzopyranopyrazoles and their macrocycles

This study presents a fast, eco-friendly, and atom-economical method for synthesis of benzopyranopyrazoles and their macrocycles in water medium using an intramolecular 1,3-dipolar cycloaddition strategy.

Polycyclic Ring Formation Using Bis-diazolactams for Cascade Stitching.

This study demonstrates the potential for creating polycyclic N-heterocycles in one pot using bis-diazolactams and rhodium(II) catalysis, with excellent diastereoselectivity in intramolecular cycloaddition reactions.

Late-stage N-functionalization of diazo NH-heterocycles: the Mitsunobu reaction vs. alkylation with alkyl halides

The Mitsunobu reaction is a promising alternative to alkylation with alkyl halides for selective N-functionalization of diazo NH-heterocycles, preserving the diazo function.