Angewandte Chemie - International Edition p. 3303 - 3307 (2011)
Update date:2022-08-02
Topics: GC-MS Column chromatography NMR spectroscopy Catalyst Ligand Stereochemistry Diastereoselective TLC (thin-layer chromatography) Anhydrous conditions Workup Oxidative Addition Reductive Elimination Reaction Optimization Inert atmosphere Schlenk technique Stoichiometric ratio Iron-mediated
Steib, Andreas K.
Thaler, Tobias
Komeyama, Kimihiro
Mayer, Peter
Knochel, Paul
trans-2-Arylcycloalcohol derivatives are obtained in high diastereoselectivity by the iron-mediated cross-coupling of cyclic TBS-protected iodohydrines with aryl Grignard reagents (see scheme; TBS=tert- butyldimethylsilyl). The stereoconvergent cross-coupling of a chiral TBS-protected 2-iodocyclohexanol provides the 2-arylcyclohexanols with no loss of stereochemical purity, and is a valuable alternative to the enantioselective opening of symmetrical epoxides. Copyright
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