One-pot Cannizzaro cascade synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl aldehydes

Burroughs, Laurence and Eccleshare, Lee and Ritchie, John and Kulkarni, Omkar and Lygo, Barry and Woodward, Simon and Lewis, William (2015) One-pot Cannizzaro cascade synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl aldehydes. Angewandte Chemie International Edition, 54 (36). pp. 10648-10651. ISSN 1521-3773

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Abstract

An intramolecular Cannizzaro-type hydride transfer to an in situ prepared allene enables the synthesis of orthofused 4-substituted cycloocta-2,5-dien-1-ones with unprecedented technical ease for an eight-ring carboannulation. Various derivatives could be obtained from commercially available (hetero)aryl aldehydes, trimethylsilylacetylene, and simple propargyl chlorides in good yields.

Item Type: Article
Keywords: aldehydes; annulation; carbocycles; medium-ring compounds; synthetic methods
Schools/Departments: University of Nottingham, UK > Faculty of Science > School of Chemistry
Identification Number: 10.1002/anie.201505347
Depositing User: Lewis, William
Date Deposited: 28 Sep 2017 11:07
Last Modified: 14 Oct 2017 08:29
URI: http://eprints.nottingham.ac.uk/id/eprint/46633

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