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Article info. : 2005; 2(4) (pp 244~337)


Enantioselective Conjugate Addition to a,b-Unsaturated Esters and Amides Mediated by Lithium Perchlorate

M.R. Saidia,*,1, R.S. Browna,* and F. Rajabib

aDepartment of Chemistry, Queen’s University, Kingston, Ontario, Canada
bDepartment of Chemistry, Department of Chemistry, Sharif University of Techology,
P. O. Box 11365-
9516 Tehran, Iran

(Received 10 September 2005, Accepted 25 September 2005)

An efficient method for the enantioselective 1,4-conjugate addition of amines to a,b-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 a,b-unsaturated amides without any side reactions.

Keywords: Enantioselective, Conjugate addition, Chiral auxiliary, Solvent-free, Unsaturated esters, Lithium perchlorate


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