Journal
ORGANIC LETTERS
Volume 15, Issue 11, Pages 2608-2611Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol4007772
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Funding
- NSFC [21172029, 21202016]
- FRFCU [10JCXK005]
- Research Fund for the Doctoral Program of Higher Education of China [RFDP 20100043120008]
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A novel and efficient method for the construction of alpha-(1,3-dithiolan-2-ylidene) delta-lactam and delta-lactone rings has been developed. It involves the reglospecific 6-endo-annulation of in situ generated 2-(1,3-dithiolan-2-ylidene)-3,4-dienamides/acids from the dehydrative coupling of alpha-oxo ketene dithioacetals with tertiary propargyl alcohols promoted by BF3 center dot Et2O. A range of alpha-(1,3-dithiolan-2-ylidene) delta-lactams and delta-lactones are obtained in good to high yields. In addition, indenes are prepared by using alpha-acetyl ketene dithioacetal as the precursor.
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