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Gosteli-Claisen Rearrangement of Propargyl Vinyl Ethers: Cascading Molecular Rearrangements

Gille, A., Rehbein, Julia and Hiersemann, Martin 2011. Gosteli-Claisen Rearrangement of Propargyl Vinyl Ethers: Cascading Molecular Rearrangements. Organic Letters 13 (8) , pp. 2122-2125. 10.1021/ol200558j

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Abstract

The ambivalent reactivity of 2-alkoxycarbonyl-substituted propargyl vinyl ethers has been explored. Depending on the conditions, the catalyzed and uncatalyzed Gosteli−Claisen rearrangement triggers downstream transformations that cascade from initially formed γ-allenyl α-keto esters to highly substituted furanes and cyclopentenes. In support of a mechanistic hypothesis, the results of a DFT study using the B1B95 and B3LYP functionals are revealed.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: American Chemical Society
ISSN: 1523-7060
Last Modified: 19 Mar 2016 22:21
URI: http://orca-mwe.cf.ac.uk/id/eprint/13007

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