An efficient asymmetric synthesis of (2S,3S)-3-trifluoromethylpyroglutamic acid

Add time:08/16/2019    Source:sciencedirect.com

The stereochemical outcome of the Michael reaction between ethyl 4,4,4-trifluorocrotonate and a Ni(II) complex of the Schiff base of glycine with (S)-o-[N-(N-benzylprolyl)amino]benzophenone was found to be subjected to kinetic and thermodynamic control. Thus, under kinetically controlled conditions high values of diastereo-selectivity, up to 94% de, allowing for an efficient asymmetric synthesis of (2S,3S)-3-trifluoromethylpyroglutamic acid, could be obtained, while the thermodynamically controlled stereoselectivity is rather modest (54–60% de).

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