Stereoselective synthesis of S-norvaline and related amino acids through a common intermediate.

Autor: Espinoza-Hicks JC; Facultad de Ciencias Químicas, Universidad Autónoma de Chihuahua, Campus Universitario 2, 31115, Chihuahua, Chih, Mexico., Chavez-Flores D; Facultad de Ciencias Químicas, Universidad Autónoma de Chihuahua, Campus Universitario 2, 31115, Chihuahua, Chih, Mexico., Zaragoza-Galan G; Facultad de Ciencias Químicas, Universidad Autónoma de Chihuahua, Campus Universitario 2, 31115, Chihuahua, Chih, Mexico., Camacho-Davila AA; Facultad de Ciencias Químicas, Universidad Autónoma de Chihuahua, Campus Universitario 2, 31115, Chihuahua, Chih, Mexico. acamach@uach.mx.
Jazyk: angličtina
Zdroj: Amino acids [Amino Acids] 2023 Jul; Vol. 55 (7), pp. 939-946. Date of Electronic Publication: 2023 Jun 09.
DOI: 10.1007/s00726-023-03289-y
Abstrakt: A divergent, enantioselective synthetic strategy is reported to produce the non-proteinogenic, biologically active natural amino acids norvaline, 5-hydroxy-4-oxo-L-norvaline, and ɣ-oxonorvaline. These were synthesized in good yields (45-75%) from the common starting material (S)-allylglycine obtained by asymmetric transfer allylation of glycine Schiff base using the Corey catalyst derived from cinchonidine in more than 97% enantiomeric excess.
(© 2023. The Author(s), under exclusive licence to Springer-Verlag GmbH Austria, part of Springer Nature.)
Databáze: MEDLINE
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