Despite being inexpensive and available in enantiopure form, Werner complexes have had no applications in enantioselective organic synthesis. This derives from their poor solubility in organic solvents and the fact that the chelating amine ligands are non-labile, preventing metal based substrate activation. However, the abundant nitrogen-hydrogen bonds could activate substrates via hydrogen bonding. The CH2Cl2-soluble  (+)-?-[Co(S,S-dpen)3](BArf)Cl2 ((+)-?-1  ) and (�)-(?)-[Co(S,S-dpen)3](BArf)Cl2 ((�)-?-1  ) have been employed in the catalytic enantioselective Michael addition of dialkyl malonates to nitroolefins with high enantioselectivity.

Werner complexes: A new paradigm in enantioselective hydrogen bond mediated catalysis

244th National Meeting (2012)

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