Skip to main content

Research Repository

Advanced Search

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

Authors

Laurence Burroughs

Lee Eccleshare

John Ritchie

Omkar Kulkarni

Barry Lygo

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
Publication Date Sep 1, 2015
Journal Angewandte Chemie International Edition
Print ISSN 1433-7851
Electronic ISSN 1521-3773
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 54
Issue 36
APA6 Citation Burroughs, L., Eccleshare, L., Ritchie, J., Kulkarni, O., Lygo, B., Woodward, S., & Lewis, W. (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), https://doi.org/10.1002/anie.201505347
DOI https://doi.org/10.1002/anie.201505347
Keywords aldehydes; annulation; carbocycles; medium-ring compounds;
synthetic methods
Publisher URL http://onlinelibrary.wiley.com/doi/10.1002/anie.201505347/abstract?
Copyright Statement Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by/4.0

Files

Burroughs_et_al-2015-Angewandte_Chemie_International_Edition.pdf (813 Kb)
PDF

Copyright Statement
Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by/4.0





You might also like



Downloadable Citations

;