Journal
ORGANIC LETTERS
Volume 11, Issue 6, Pages 1229-1231Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol900029d
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Funding
- Natural Sciences and Engineering Research Council of Canada
- Killam Foundation
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Treatment of an allenyl vinyl ketone with trifluoroacetic acid leads to Nazarov cyclization, and the intermediate carbocation is trapped efficiently by trifluoroacetate. Hydrolysis of the ester with methanol and basic alumina provides, in good to excellent overall yield, a 5-hydroxycyclopent-2-enone in which the alcohol is predominantly trans to a substituent at C-4.
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