Enantioselective copper-catalyzed allylic alkylation with dialkylzincs using phosphoramidite ligands.

TitleEnantioselective copper-catalyzed allylic alkylation with dialkylzincs using phosphoramidite ligands.
Publication TypeJournal Article
Year of Publication2001
AuthorsMalda H, van Zijl AW, Arnold LA, Feringa BL
JournalOrganic letters
Volume3
Issue8
Pagination1169-71
Date Published2001 Apr 19
Abstract

[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 JournalOrg. Lett.