Macrocyclic Iron(II) Hydrides as Catalysts for Base-Free Asymmetric Transfer Hydrogenation

Luca, Lorena De

doi:10.3929/ethz-b-000377546

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“…However, preliminary tests with 1-(4-fluorophenyl)-2-(2-methoxyphenyl)ethane-1,2dione as a substrate have shown low regioselectivity (1:1.5 ratio). 38 Next, we investigated the role of molecular sieves in the outcome of the reaction. Water, Base, or Both?…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Concerning the limitations of the method, we have prepared an N 2 P 2 macrocycle bearing mesityl substituents instead of phenyl on the P atoms to optimize the stereoselection with unsymmetrically substituted benzils. However, preliminary tests with 1-(4-fluorophenyl)-2-(2-methoxyphenyl)ethane-1,2-dione as a substrate have shown low regioselectivity (1:1.5 ratio) . Next, we investigated the role of molecular sieves in the outcome of the reaction.…”

Section: Results and Discussionmentioning

confidence: 99%

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Chiral Benzoins via Asymmetric Transfer Hemihydrogenation of Benzils: The Detail that Matters

Luca

Mezzetti

2020

J. Org. Chem.

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The synthesis of enantiomerically pure benzoins by hydrogenation of readily available benzils has been long thwarted by their base-sensitivity. We show here that an iron(II) hydride complex catalyzes the asymmetric transfer hydrogenation of benzils from 2-propanol. When strictly base-free conditions are granted, excellent enantioselectivity is achieved even with o-substituted substrates, which are particularly challenging to prepare with other methods. Hence, under optimized reaction conditions, chiral benzoins were prepared in good yields (up to 83%) and excellent enantioselectivity (up to 98% ee) in short reaction times (30–75 min). Also, this work confirms that both enantiomers of the benzoin products can be accessed when a metal catalyst is used, which is a clear advantage over enzymatic methods.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Results and Discussionmentioning

confidence: 99%