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

✍ Scribed by Vadim A Soloshonok; Dimitry V Avilov; Valery P Kukhar'; Luc Van Meervelt; Nikolai Mischenko

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 152 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)01054-x

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✦ Synopsis

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)aminolbenzophenone was found to be subjected to kinetic and thermodynamic control. Thus, under kinetically controlled conditions high values of diastereoselectivity, 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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