23277-00-1Relevant articles and documents
Stereoselective synthesis of 2(S)-(1,1-dimethylethylsulfonylmethyl)-3-(1- naphthyl)-propionic acid, building block for protease inhibitors via asymmetric hydrogenation
Beck,Jendralla,Kammermeier
, p. 4691 - 4698 (1994)
Title compound 1b (purity > 99%, 99.6% ee) is synthesized (100g scale) from commercial 3-bromo-pyruvic acid in six steps with an overall yield of 16%. The sequence is operationally simple and devoid of chromatographic purifications. Key step is the asymmetric hydrogenation of a substrate with sulfur functionality.
Stereopure Functionalized Benzosultams via Ruthenium(II)-Catalyzed Dynamic Kinetic Resolution-Asymmetric Transfer Hydrogenation
Jeran, Marko,Cotman, Andrej Emanuel,Stephan, Michel,Mohar, Barbara
supporting information, p. 2042 - 2045 (2017/04/28)
A 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.
Process for the stereoselective synthesis of 3-substituted 2-sulfonylmethylpropionic acids, and intermediate products
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, (2008/06/13)
Compounds of the formula I STR1 can be prepared in a multi-day process starting from the compounds of the formulae II and III