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Synthesis 2016; 48(14): 2213-2225
DOI: 10.1055/s-0035-1560441
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
Further Information
Publication History
Received: 18 December 2015
Accepted after revision: 26 February 2016
Publication Date:
13 April 2016 (online)
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) acetateSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560441.
- Supporting Information
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