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Preparation of Enantiomerically Pure β,β‐Diaryl β‐Hydroxy‐α‐Amino Acids and Evaluation of Their Potential as Organocatalysts
Author(s) -
Arimitsu Satoru,
Oshiro Koki,
Endo Katsuki,
Gima Emi,
Poorsadeghi Samira
Publication year - 2020
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900694
Subject(s) - chemistry , oxazolidine , amino acid , reagent , decomposition , organic chemistry , enantioselective synthesis , organocatalysis , catalysis , combinatorial chemistry , biochemistry
A general synthetic procedure was developed for enantiomerically pure β,β‐diaryl β‐hydroxy‐α‐amino acids 5 , starting from readily available oxazolidine ester 1 and a wide variety of Grignard reagents. The problematic oxidative decomposition of β‐aminodiols 3 , due to their instability in the presence of metallic oxidants, was successfully suppressed using Parikh‐Doering oxidation and subsequent Pinnick oxidation. Additionally, the organocatalytic ability of β,β‐diaryl β‐hydroxy‐α‐amino acids 5 was evaluated with respect to asymmetric fluorination of 2‐phenylpropionaldehyde 6 , and moderate enantioselectivity, 61%, was achieved using compound 5 f .