Blakemore, Caroline A. published the artcileScalable, telescoped hydrogenolysis-enzymic decarboxylation process for the asym. synthesis of (R)-α-heteroaryl propionic acids, SDS of cas: 884495-13-0, the publication is Organic Process Research & Development (2021), 25(3), 421-426, database is CAplus.
Enantiopure α-aryl propionic acids are useful building blocks for pharmaceutical research and can be accessed enzymically using arylmalonate decarboxylases (AMDases) from the corresponding malonic acids. However, the intrinsic instability of malonic acids is a major drawback to this approach in which spontaneous decarboxylation can occur, subsequently eroding enantioselectivity and giving rise to racemic products. This was particularly evident for a panel of N-heterocyclic propionic acids that we wished to access using the approach. Herein, we describe a process to overcome the spontaneous decarboxylation problem in which hydrogenolysis of the corresponding dibenzyl malonates was performed in a biphasic toluene-basic aqueous buffer mixture and telescoped into the subsequent AMDase step. This procedure enabled compounds to be accessed in high enantioselectivities and was successfully demonstrated on 120 g with high yield (76%) and ee (98%).
Organic Process Research & Development published new progress about 884495-13-0. 884495-13-0 belongs to iodides-buliding-blocks, auxiliary class Pyridine,Fluoride,Iodide,Ether, name is 5-Fluoro-4-iodo-2-methoxypyridine, and the molecular formula is C6H5FINO, SDS of cas: 884495-13-0.
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