Chiral Cyclobutanols and Cyclopentane Dimers via Samarium(II) Iodide Induced Keto-Olefin Cyclisations of Carbohydrate-Derived Unsaturated Ketones

Abstract Some pentose and hexose sugars were converted into unsaturated ketone derivatives, which themselves served as substrates for 4-EXO-TRIG radical cyclisation reactions mediated by SmI 2 . Depending on the order of addition of reagents, the keto-olefins could also be made to undergo a surprisi...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2009-06, Vol.2009 (12), p.2009-2014
Main Authors: Williams, D. Bradley, Caddy, Judy, Blann, Kevin, Grové, J. J., Holzapfel, Cedric W.
Format: Article
Language:English
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Summary:Abstract Some pentose and hexose sugars were converted into unsaturated ketone derivatives, which themselves served as substrates for 4-EXO-TRIG radical cyclisation reactions mediated by SmI 2 . Depending on the order of addition of reagents, the keto-olefins could also be made to undergo a surprising tandem 5-ENDO-TRIG cyclisation/dimerisation reaction to a cyclopentane dimer or a cyclobutane monomer.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0029-1216824