153077-61-3Relevant academic research and scientific papers
Asymmetric Steering of the Pictet-Spengler Reaction by Means of Amino Acid Esters as Chiral Auxiliary Groups
Waldmann, Herbert,Schmidt, Gunther,Jansen, Martin,Geb, Jutta
, p. 11865 - 11884 (1994)
N-β-(3-Indolyl)ethyl amino acid esters and differently substituted aromatic aldehydes in the presence of acetic acid form iminium intermediates which at 6 degC to 40 degC undergo Pictet-Spengler cyclizations to give tetrahydro-β-carbolines with diastereomer ratios up to 98.5:1.5.The chiral auxiliary group is removed from the heterocycles by employing a retro Strecker reaction as the key transformation.
