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Mac-H: Asymmetric Hydrogenation in a Bottle

Chemfiles Volume 7 Article 5

MacMillan and co-workers have reported the combination of MacMillan Imidazolidinone OrganoCatalysts and Hantzsch esters to facilitate the first enantioselective organocatalytic hydride reduction of a, b-unsaturated aldehydes.1 Interestingly, isomerically pure E- and Z-olefin substrates will be reduced to the same enantiomer, allowing the researcher to use geometrically impure enals while maintaining excellent enantioselectivity. (S)-Mac-H is a convenient 6:1 formulation of the ethyl Hantzsch ester and OrganoCatalyst 1 for asymmetric reductions.

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  1. Ouellet, S. G. et al. J. Am. Chem. Soc., 2005, 127, 32.

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