title: Cobalt-mediated diastereoselective cross-coupling reactions between cyclic halohydrins and arylmagnesium reagents.
abstract: Cyclic TBS-protected iodohydrins (and bromohydrins) undergo a highly diastereoselective cross-coupling with various aryl- and heteroarylmagnesium reagents in the presence of THF-soluble CoCl2·2LiCl and TMEDA as a ligand leading to trans-2-arylcyclohexanol derivatives in good yields and dr up to >99:1. A range of functional groups are tolerated in the Grignard reagent (e.g., COOR, CN, CF3, SF5). The use of heterocyclic iodohydrins leads to trans-3,4-disubstituted pyrrolidines and tetrahydrofurans.
authors.affiliation: Department of Chemistry, Ludwig-Maximilians-Universität München , Butenandtstr. 5-13, Haus F, 81377 Munich, Germany.
authors.forename: Jeffrey M
authors.initials: JM
authors.lastname: Hammann
authors.forename: Andreas K
authors.initials: AK
authors.lastname: Steib
authors.forename: Paul
authors.initials: P
authors.lastname: Knochel