1042980-75-5Relevant academic research and scientific papers
Enantioselective total synthesis of (S)-(-)-quinolactacin B
Shankaraiah, Nagula,da Silva, Wender A.,Andrade, Carlos Kleber Z.,Santos, Leonardo Silva
, p. 4289 - 4291 (2008)
The enantioselective total synthesis of (-)-quinolactacin B (-)-1 was performed in seven steps and 33% overall yield from tryptamine. The synthesis features the use of ruthenium catalytic asymmetric hydrogen reaction to introduce the chirality in dihydro-
An efficient synthetic approach to optically active β-carboline derivatives via Pictet-Spengler reaction promoted by trimethylchlorosilane
Tsuji, Riichiro,Nakagawa, Masako,Nishida, Atsushi
, p. 177 - 180 (2003)
A highly diastereoselective Pictet-Spengler reaction using chiral tryptamine carbamates has been developed. The reaction proceeds using aromatic and aliphatic aldehydes in the presence of trimethylchlorosilane.
Palladium asymmetric reduction of β-carboline imines mediated by chiral auxiliaries assisted by microwave irradiation
Espinoza-Moraga, Marlene,Caceres, Ana Gloria,Santos, Leonardo Silva
scheme or table, p. 7059 - 7061 (2010/02/28)
An alternative synthetic approach for the introduction of chirality in β-carboline moiety through in situ reduction of N-acyliminium ion intermediates generated from imine 2 and chloroformate of 8-phenylmenthyl as chiral auxiliary was achieved. The method applied microwave-assisted irradiation and used PdCl2/Et3SiH protocol as a mild reducing agent, which decreased reaction times to minutes when compared to the conventional thermal reactions. The diastereoselectivity (4-12:1) of the reduction produced R-amines, which were assigned after chiral auxiliary removal and spectroscopic data compared to products obtained from Noyori asymmetric hydrogenation catalyst.
