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Org Lett. 2013 Jun 7;15(11):2608-11. doi: 10.1021/ol4007772. Epub 2013 May 13.

Regiospecific 6-endo-annulation of in situ generated 3,4-dienamides/acids: synthesis of δ-lactams and δ-lactones.

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  • 1Department of Chemistry, Northeast Normal University, Changchun 130024, PR of China.

Abstract

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.

PMID:
23668368
DOI:
10.1021/ol4007772
[PubMed - indexed for MEDLINE]
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