47672-25-3Relevant 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.
Highly stereoselective syntheses of syn- and anti-1,2-amino alcohols
Hoffman, Robert V.,Maslouh, Najib,Cervantes-Lee, Francisco
, p. 1045 - 1056 (2007/10/03)
The reduction of N-protected amino ketones can be carried stereoselectively to produce either the syn- or anti-amino alcohol diastereomer. Carbamate-protected amino ketones can be reduced predictably and selectively to anti-amino alcohols with LiAlH(O-t-Bu)3 in ethanol at -78°C. N-Trityl-protected amino ketones can be reduced selectively to syn-amino alcohols with LiAlH(O-t-Bu)3 in THF at -5°C.
Efficient Synthesis of N-Triphenylmethyl α-Amino Acids
Mutter, Manfred,Hersperger, Rene
, p. 198 - 200 (2007/10/02)
A new one-pot synthesis of N-triphenylmethyl(trityl) α-amino acids 3 via their trityl ester 2 has been developed.
Efficient "One-Pot" Synthesis of N-Trityl Amino Acids
Barlos, Kleomenis,Papaioannou, Dionysios,Theodoropoulos, Dimitrios
, p. 1324 - 1326 (2007/10/02)
A sequential procedure has been developed whereby neutral amino acids 1 were tritylated via their corresponding trimethylsilyl esters 2 to afford, after mild hydrolysis, N-trityl amino acids 3 in high yields and purity.Hydroxy amino acids 4 were preferent
