111060-54-9Relevant articles and documents
Chiral ferrocenyl amino alcohols as catalysts for the enantioselective borane reduction of ketones
Brunin, Thierry,Cabou, Jerome,Bastin, Stephanie,Brocard, Jacques,Pelinski, Lydie
, p. 1241 - 1243 (2002)
The catalytic asymmetric borane reduction of prochiral ketones was examined in the presence of chiral oxazaborolidine catalysts prepared in situ from chiral ferrocenyl amino alcohols. The corresponding chiral secondary amino alcohols were obtained with modest to high enantiomeric excesses (up to 90%) using (1S,2S)-2-amino-1-ferrocenyl-3,3-dimethyl-1-butanol 5c.
Hydrogen-Borrowing Alkylation of 1,2-Amino Alcohols in the Synthesis of Enantioenriched γ-Aminobutyric Acids
Hall, Christopher J. J.,Goundry, William R. F.,Donohoe, Timothy J.
, p. 6981 - 6985 (2021/03/01)
For the first time we have been able to employ enantiopure 1,2-amino alcohols derived from abundant amino acids in C?C bond-forming hydrogen-borrowing alkylation reactions. These reactions are facilitated by the use of the aryl ketone Ph*COMe. Racemisation of the amine stereocentre during alkylation can be prevented by the use of sub-stoichiometric base and protection of the nitrogen with a sterically hindered triphenylmethane (trityl) or benzyl group. The Ph* and trityl groups are readily cleaved in one pot to give γ-aminobutyric acid (GABA) products as their HCl salts without further purification. Both steps may be performed in sequence without isolation of the hydrogen-borrowing intermediate, removing the need for column chromatography.
Regioselective Fluorination of α-Hydroxy-β-aminophosphonates by Using PyFluor
Ka?mierczak, Marcin,Kubicki, Maciej,Koroniak, Henryk
, p. 3844 - 3852 (2018/07/31)
We report a simple protocol for the synthesis of α-fluoro-β-aminophosphonates by the regioselective fluorination of α-hydroxy-β-aminophosphonates under mild conditions. The fluorination reactions were mediated by the PyFluor reagent and occurred with the retention of configuration. The main products of this reaction were a series of α-fluoro-β-aminophosphonates, which can be used as precursors in the preparation of medicinally important compounds (e.g., dipeptide analogues).
