Cobalt-mediated diastereoselective cross-coupling reactions between cyclic halohydrins and arylmagnesium reagents
Jeffrey M Hammann1, Andreas K Steib, Paul Knochel
1Department of Chemistry, Ludwig-Maximilians-Universität München , Butenandtstr. 5-13, Haus F, 81377 Munich, Germany.
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.
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