A highly efficient enantioselective synthesis for the potent G-protein-coupled receptor 40 agonist MK-2305 was developed. The key tetrasubstituted olefin was prepared via a stereoselective Mukaiyama aldol reaction/elimination sequence. The highly… Click to show full abstract
A highly efficient enantioselective synthesis for the potent G-protein-coupled receptor 40 agonist MK-2305 was developed. The key tetrasubstituted olefin was prepared via a stereoselective Mukaiyama aldol reaction/elimination sequence. The highly enantioselective rhodium-catalyzed transfer hydrogenation of the tetrasubstituted olefin afforded the target compound MK-2305 in excellent optical and chemical purity. The key asymmetric transfer hydrogenation proceeds in excellent yields and enantioselectivities for a variety of substrates. The superior reactivity of the tethered catalysts was revealed by NMR studies.
               
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