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Enantioselective copper-catalyzed allylic alkylation with dialkylzincs using phosphoramidite ligands.
|Title||Enantioselective copper-catalyzed allylic alkylation with dialkylzincs using phosphoramidite ligands.|
|Publication Type||Journal Article|
|Year of Publication||2001|
|Authors||Malda H, van Zijl AW, Arnold LA, Feringa BL|
|Date Published||2001 Apr 19|
[reaction: see text]. In the presence of a catalytic amount of copper salts, cinnamyl halides undergo a regio- and enantioselective S(N)2' alkylation with dialkylzincs using chiral phosphoramidites as ligands. An S(N)2':S(N)2 ratio of 85:15 and enantiomeric excesses up to 77% for the chiral S(N)2' products are found. Variation of solvent and reaction temperature revealed that the highest regio- and enantioselectivities are found using coordinating solvents of -40 degrees C.
|Alternate Journal||Org. Lett.|