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

Sengodagounder Muthusamy; Chinnakuzhanthai Gangadurai

doi:10.1055/s-0035-1560441

Synthesis, Table of Contents

Synthesis 2016; 48(14): 2213-2225
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

Authors

Sengodagounder Muthusamy*

School of Chemistry, Bharathidasan University, Tiruchirappalli, 620024, India Email: muthu@bdu.ac.in
Chinnakuzhanthai Gangadurai

School of Chemistry, Bharathidasan University, Tiruchirappalli, 620024, India Email: muthu@bdu.ac.in

Abstract

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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.

Key words

bis-diazo compounds - domino reactions - diastereoselectivity - X–H insertion - isomünchnones - rhodium(II) acetate

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References

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Supplementary Material

Supporting Information (PDF)