Synthesis of chiral allenes from ynamides through a highly stereoselective Saucy-Marbet rearrangement |
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| Authors: | Kimberly CM Kurtz |
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| Institution: | Division of Pharmaceutical Sciences, Department of Chemistry, University of Wisconsin, Madison, WI 53705 USA |
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| Abstract: | A highly stereoselective Saucy-Marbet rearrangement using chiral ynamides and propargyl alcohols is described here. This rearrangement can be catalyzed by para-nitrobenzenesulfonic acid and leads to high diastereoselectivities for a range of different chiral propargyl alcohols and ynamides in a stereochemically intriguing matched, mismatched or indifferent manner. The stereoselective Saucy-Marbet rearrangement of ynamides provides an excellent entry to highly substituted chiral homo allenyl alcohols. |
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| Keywords: | Ynamides Saucy-Marbet rearrangement Chiral allenes Sibi and Evans' auxiliaries Axial chirality |
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