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. Author manuscript; available in PMC: 2009 Mar 18.
Published in final edited form as: Nature. 2008 Sep 18;455(7211):323–332. doi: 10.1038/nature07370

Figure 2. Asymmetric hydrogenation of β-enamino amides toward Januvia® (8).

Figure 2

The rapid and selective synthesis of β-enamino amide 3 enabled a key rhodium/5-catalyzed enantioselective hydrogenation under mildly acidic conditions to directly reveal the β-amino amide in Merck's synthesis of Januvia®, an FDA-approved treatment for type II diabetes.36,39 DMAP, 4-(N,N-dimethylamino)pyridine; DMA, N,N-dimethylacetamide; PivCl, pivaloyl chloride; COD, cyclooctadiene. (Reduced to 45%)