100897-59-4Relevant academic research and scientific papers
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.
supporting information, 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.
Preparation of Tritylamino Alcohols
Barlos, Kleomenis,Papaioannou, Dionysios,Patrianakou, Stella,Tsegenidis, Theodoros
, p. 952 - 956 (2007/10/02)
N-Tritylamino acid trimethylsilyl esters 2 were mildly reduced with LiAlH4 to give N-tritylamino alcohols 3 in high yields and purity.Other methods provided 3 in lower yields.
