Journal
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY
Volume 2, Issue 4, Pages 300-304Publisher
SPRINGER
DOI: 10.1007/BF03245934
Keywords
enantioselective; conjugate addition; chiral auxiliary; solvent-free; unsaturated esters; lithium perchlorate
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An efficient method for the enantioselective 1,4-conjugate addition of amines to alpha,beta-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 alpha,beta-unsaturated amides without any side reactions.
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