Enantioselective Conjugate Addition to α,β-Unsaturated Esters and
Amides Mediated by Lithium Perchlorate

M.R. Saidi^a,^,1, R.S. Brown^a,* and F. Rajabi^b*

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

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.

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

Enantioselective Conjugate Addition to α,β-Unsaturated Esters andAmides 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 Technology, P. O. Box 11365- 9516 Tehran, Iran

Enantioselective Conjugate Addition to α,β-Unsaturated Esters and
Amides Mediated by Lithium Perchlorate

M.R. Saidi^a,^,1, R.S. Brown^a,* and F. Rajabi^b*

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