Hydrogen‐Borrowing Alkylation of 1,2‐Amino Alcohols in the Synthesis of Enantioenriched γ‐Aminobutyric Acids

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 use of aryl ketone Ph*COMe. Racemisation amine stereocentre during can be prevented sub-stoichiometric base and protection nitrogen with a sterically hindered triphenylmethane (trityl) or benzyl group. The Ph* trityl groups readily cleaved one pot give γ-aminobutyric acid (GABA) products as their HCl salts without further purification. Both steps may performed sequence isolation intermediate, removing need for column chromatography.