Enantioselective conjugate addition to α,β-unsaturated esters and amides mediated by lithium perchlorate |
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Authors: | M R Saidi R S Brown F Rajabi |
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Institution: | 1. Department of Chemistry, Queen’s University, Kingston, Ontario, Canada 2. Department of Chemistry, Department of Chemistry, Sharif University of Technology, P. O. Box 11365-9516, Tehran, Iran
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Abstract: | An efficient method for the enantioselective 1,4-conjugate addition of amines to α,β-unsaturated esters containing an inexpensive chiral auxiliary, such as (S)-2-methyl-1-butanol and fenchyl alcohol, in solvent-free conditions mediated by solid lithium perchlorate is reported. Over 12 examples of the products are generated in excellent yields, accompanied by moderate enantioselectivity. The concentrated solution of LiClO4 in a diethyl ether system works well for the enantioselective 1,4-addition of organolithium compounds to α,β-unsaturated amides without any side reactions. |
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