10.1021/acs.orglett.7b00670.s002
Marko Jeran
Marko
Jeran
Andrej Emanuel Cotman
Andrej Emanuel
Cotman
Michel Stephan
Michel
Stephan
Barbara Mohar
Barbara
Mohar
Stereopure Functionalized Benzosultams via Ruthenium(II)-Catalyzed
Dynamic Kinetic Resolution–Asymmetric Transfer Hydrogenation
American Chemical Society
2017
Ru
enantiopure ansa
DKR
Hydrogenation
TsDPEN
enantioselective
ligand
mix
hydrogenation
4 Ph
yn
sulfonylamino
ULTAM
ee
stereopure
hydroxy-arylmethyl
access
DPEN
-3-phenyl
syn
HCO
isomer trans -4-
Ruthenium
transfer
aminobenzyl
Transfer
conversion
diastereo
aryl ketones
application
II
4- hydroxy-benzo -δ-
Dynamic
sulfonylimino
10 000
Kinetic
Stereopure Functionalized Benzosultams
2017-04-13 17:18:34
Dataset
https://acs.figshare.com/articles/dataset/Stereopure_Functionalized_Benzosultams_via_Ruthenium_II_-Catalyzed_Dynamic_Kinetic_Resolution_Asymmetric_Transfer_Hydrogenation/4873568
A highly diastereo-
and enantioselective Ru(II)-catalyzed dynamic
kinetic resolution–asymmetric transfer hydrogenation (DKR–ATH)
of α-(<i>N</i>-sulfonylimino) and α-(<i>N</i>-sulfonylamino) aryl ketones to 4-hydroxy-benzo-δ-
and 3-(α-hydroxy-arylmethyl)-benzo-γ-sultams is presented.
By employing enantiopure <i>ansa</i>-Ru[PipSO<sub>2</sub>DPEN(CH<sub>2</sub>)<sub>4</sub>Ph] <b>cat. II</b> with S/C
= 10 000 in a HCO<sub>2</sub>H/Et<sub>3</sub>N 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” <i>N</i>,<i>N</i>-ligand
s<i>yn</i>-3-(α-aminobenzyl)-benzo-γ-sultam
(“<i>syn</i>-ULTAM”) and its structural isomer <i>trans</i>-4-amino-3-phenyl-benzo-δ-sultam (<i>trans</i>-<b>4</b>) is demonstrated.