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Regiospecific 6-Endo-Annulation of in Situ Generated 3,4-Dienamides/Acids: Synthesis of δ-Lactams and δ-Lactones

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Department of Chemistry, Northeast Normal University, Changchun 130024, P. R. of China, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China, and School of Chemistry and Life Science, Anshan Normal University, Anshan, Liaoning 114007, P. R. of China
[email protected]; [email protected]
†Northeast Normal University.
§Anshan Normal University.
‡Nankai University.
Cite this: Org. Lett. 2013, 15, 11, 2608–2611
Publication Date (Web):May 13, 2013
https://doi.org/10.1021/ol4007772
Copyright © 2013 American Chemical Society
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    Abstract

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    A novel and efficient method for the construction of α-(1,3-dithiolan-2-ylidene) δ-lactam and δ-lactone rings has been developed. It involves the regiospecific 6-endo-annulation of in situ generated 2-(1,3-dithiolan-2-ylidene)-3,4-dienamides/acids from the dehydrative coupling of α-oxo ketene dithioacetals with tertiary propargyl alcohols promoted by BF3·Et2O. A range of α-(1,3-dithiolan-2-ylidene) δ-lactams and δ-lactones are obtained in good to high yields. In addition, indenes are prepared by using α-acetyl ketene dithioacetal as the precursor.

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    Experimental procedures; 1H NMR, 13C NMR, HSQC, and HMBC spectroscopic data for all compounds. This material is available free of charge via the Internet at http://pubs.acs.org.

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