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Stereopure Functionalized Benzosultams via Ruthenium(II)-Catalyzed Dynamic Kinetic Resolution–Asymmetric Transfer Hydrogenation
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posted on 2017-04-13, 17:18 authored by Marko Jeran, Andrej Emanuel Cotman, Michel Stephan, Barbara MoharA highly diastereo-
and enantioselective Ru(II)-catalyzed dynamic
kinetic resolution–asymmetric transfer hydrogenation (DKR–ATH)
of α-(N-sulfonylimino) and α-(N-sulfonylamino) aryl ketones to 4-hydroxy-benzo-δ-
and 3-(α-hydroxy-arylmethyl)-benzo-γ-sultams is presented.
By employing enantiopure ansa-Ru[PipSO2DPEN(CH2)4Ph] cat. II with S/C
= 10 000 in a HCO2H/Et3N binary mix,
up to >99.9% ee and dr >99:1 are obtained with 100% conversion
under
mild conditions. Application to access the stereopure “structurally
simplified TsDPEN” N,N-ligand
syn-3-(α-aminobenzyl)-benzo-γ-sultam
(“syn-ULTAM”) and its structural isomer trans-4-amino-3-phenyl-benzo-δ-sultam (trans-4) is demonstrated.
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Ruenantiopure ansaDKRHydrogenationTsDPENenantioselectiveligandmixhydrogenation4 PhynsulfonylaminoULTAMeestereopurehydroxy-arylmethylaccessDPEN-3-phenylsynHCOisomer trans -4-RutheniumtransferaminobenzylTransferconversiondiastereoaryl ketonesapplicationII4- hydroxy-benzo -δ-Dynamicsulfonylimino10 000KineticStereopure Functionalized Benzosultams
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