Chiral NADH models with restricted or blocked rotation at the amide function: attempts to interpret the mechanism of the enantioselective hydrogen transfer to Methyl benzoylformate (cas 15206-55-0)

Add time:07/28/2019    Source:sciencedirect.com

Various NADH models with the following characteristics were studied and compared with previously reported models: (1) use of (S)-phenylalaninol as chiral auxiliary; (2) orientation in or out of the plane of the amide carbonyl. Despite the occurrence of apparently similar characteristics, they gave very different results in the asymmetric reduction of methyl benzoylformate. A detailed NMR study was performed in order to explain the behaviour of these models.

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