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- Title
One-Pot Preparation of Enantiopure Fluorinated β-Amino Acid Precursors.
- Authors
Jones, Joshua H.; Appayee, Chandrakumar; Brenner‐Moyer, Stacey E.
- Abstract
Chiral β-fluoro amines and β,β-difluoro amines are common substructures in medicinal compounds. Industrial syntheses typically use enantiopure starting materials, chiral auxiliaries, or the resolution of enantiomeric or diastereomeric mixtures to install these functionalities in enantiopure form. With the goal of improving access to these substructures, we recently developed the first catalytic enantioselective olefin aminohalogenation reaction, which produced chiral β-fluoro amines in a single flask from achiral enal starting materials. This paper describes the extension of this method to the preparation of β-amino-α,α-difluoro carbonyl compounds. Specifically, carbon-nitrogen and carbon-fluorine bond-forming reactions were combined in an organocascade reaction to produce β-amino-α,α-difluoro carbonyl compounds containing alkyl substituents at the β-position. As such, this method is mechanistically distinct from, and complementary to, existing one-pot catalytic enantioselective methods for the preparation of fluorinated β-amino acid precursors.
- Subjects
AMINO acids; ORGANOCATALYSIS; CHEMICAL synthesis; FLUORINE; AMINES
- Publication
European Journal of Organic Chemistry, 2014, Vol 2014, Issue 24, p5273
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201402369