New Chiral Hydrogenation Technology
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Leverkusen - Bayer AG has commercialized a new chiral hydrogenation technology to meet the demand for chiral advanced intermediates and active pharmaceutical ingredients with one or more stereo-centers. The technology allows Bayer to produce chiral hydrogenation catalysts including the R and S version of Bayer's proprietary ligand Cl-MeO-BIPHEP, formally known as (R) and (S)-5,5'-Dichloro-6,6'-dimethoxy-2,2'-bis(diphenylphosphino)-1,1'-biphenyl. Cl-MeO-BIPHEP forms organometallic complexes with the transition metals ruthenium and rhodium. The ruthenium complex is an especially versatile catalyst for the efficient enantioselective hydrogenation (ee often greater than 99 percent) of CO and CC double-bonded substrates. Bayer launched the technology in late 2001 in one of its processes and is now using this ligand to perform a multi-ton enantioselective hydrogenation.
To promote Cl-MeO-BIPHEP in the international R&D community, Bayer AG has entered into agreement with Strem Chemicals, Inc. to market the ligand in research quantities. Strem, with U.S. headquarters in Newburyport, Mass., is a leading manufacturer and marketer of R&D chemicals. The company is currently selling and shipping orders for the R and S versions of Cl-MeO-BIPHEP (CAS No. 185913-98-8 and 185913-97-7).
Bayer's new synthesis allows the introduction of a wide spectrum of substituents (R-groups) in place of the phenyl group on the phosphorous. "This allows us to fine tune the catalyst more efficiently than was possible before. Previously, the racemic separation took place after the R group was attached. That required working out a separate resolution for each R group," Rudolph Hanko, head of Bayer's Fine Chemicals Business Unit, said. In addition to custom manufacturing, Bayer's Fine Chemicals Business Unit offers its customers process development services. These include finding the most suitable catalyst.
For enantioselective hydrogenation processes, complexes with Cl-MeO-BIPHEP are but one of many possible catalysts. Using fast screening technology, Bayer can quickly and efficiently find the optimal catalyst and reaction conditions. In addition to chiral hydrogenation, Bayer offers its customers access to other advanced chiral technologies. These including Simulated Moving Bed chromatography, crystallization-induced resolution, enzymatic conversion and stereo-specific synthesis.
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