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Dynamic kinetic resolution of α-keto esters via asymmetric transfer hydrogenation.

ABSTRACT: The dynamic kinetic resolution of β-aryl α-keto esters has been accomplished using a newly designed (arene)RuCl(monosulfonamide) transfer hydrogenation catalyst. This dynamic process generates three contiguous stereocenters with remarkable diastereoselectivity through a reduction/lactonization sequence. The resulting enantioenriched, densely functionalized γ-butyrolactones are of high synthetic utility, as highlighted by several secondary derivatizations.

SUBMITTER: Steward KM

PROVIDER: S-EPMC3342478 | biostudies-literature | 2012 May

REPOSITORIES: biostudies-literature

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Dynamic kinetic resolution of α-keto esters via asymmetric transfer hydrogenation.

Steward Kimberly M KM Gentry Emily C EC Johnson Jeffrey S JS

Journal of the American Chemical Society 20120417 17

The dynamic kinetic resolution of β-aryl α-keto esters has been accomplished using a newly designed (arene)RuCl(monosulfonamide) transfer hydrogenation catalyst. This dynamic process generates three contiguous stereocenters with remarkable diastereoselectivity through a reduction/lactonization sequence. The resulting enantioenriched, densely functionalized γ-butyrolactones are of high synthetic utility, as highlighted by several secondary derivatizations. ...[more]

PMID: 22509806

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