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

Burroughs, Laurence; Eccleshare, Lee; Ritchie, John; Kulkarni, Omkar; Lygo, Barry; Woodward, Simon; Lewis, William

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


Authors

Laurence Burroughs

Lee Eccleshare

John Ritchie

Omkar Kulkarni

Barry Lygo

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SIMON WOODWARD simon.woodward@nottingham.ac.uk
Professor of Synthetic Organic Chemistry

William Lewis



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.

Journal Article Type Article
Acceptance Date Jul 29, 2015
Online Publication Date Aug 25, 2015
Publication Date Sep 1, 2015
Deposit Date Sep 28, 2017
Publicly Available Date Sep 28, 2017
Journal Angewandte Chemie International Edition
Print ISSN 1433-7851
Electronic ISSN 1521-3773
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 54
Issue 36
DOI https://doi.org/10.1002/anie.201505347
Keywords aldehydes; annulation; carbocycles; medium-ring compounds;
synthetic methods
Public URL https://nottingham-repository.worktribe.com/output/757860
Publisher URL http://onlinelibrary.wiley.com/doi/10.1002/anie.201505347/abstract?

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