Diels-Alder reactions of cyclic isoimidium salts are described. The corresponding cycloadducts are obtained with high regio- and stereoselectivity. The use of homochiral cyclic isoimidium salts delivers cycloadducts with excellent diastereoselectivity (>99:1) that can be efficiently converted to enantiomerically pure lactones.
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Regiospecific Ficini [2 + 2] cycloaddition of ynamides with cyclic isoimidium salts under catalyst-free conditions.
Org Lett
August 2014
Key Laboratory of Synthetic and Natural Functional Molecular Chemistry of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an 710069, China.
The regiospecific [2 + 2] cycloaddition of cyclic isoimidium salts with ynamides is described. This effort led to the development of the first successful example of a catalyst-free, thermally driven Ficini [2 + 2] cycloaddition process of ynamides with α,β-unsaturated carbonyl compounds, giving the stable cyclobutenamides in excellent yields (up to 99%).
View Article and Find Full Text PDFDiels-Alder reactions of cyclic isoimidium salts.
Org Lett
October 2010
Department of Chemistry, University of Rochester, Rochester, New York 14627-0216, USA.
Diels-Alder reactions of cyclic isoimidium salts are described. The corresponding cycloadducts are obtained with high regio- and stereoselectivity. The use of homochiral cyclic isoimidium salts delivers cycloadducts with excellent diastereoselectivity (>99:1) that can be efficiently converted to enantiomerically pure lactones.
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