RT Journal Article
T1 Diastereoselective C-alkylation of aldimines, derived from chiral alpha-carbon heteroatom substituted aldehydes, with triethylborane. Application to the synthesis of benzylisoquinolines
A1 Fuentes-Ríos, David
A1 Muñoz, Carmen
A1 Díaz-Morilla, Amelia
A1 Sarabia-García, Francisco Ramón
A1 López-Romero, Juan Manuel
K1 Aminas
AB The one-pot reaction of a chiral aldehyde, p-methoxyaniline or p-fluoroaniline, and triethylborane produces the corresponding alkylated chiral amine with high yields and distereoisomeric ratios. Stereocontrol is induced by the presence of a heteroatom in the alfa-position to the aldehyde. In case of alkylation of imines derived from chiral aliphatic amines, good yields and moderate to high diastereoselectivity are obtained: yields are significantly better when the preformed imine is used in the reaction with triethyl borane, and diastereoselectivity of the reactions is largely depending on the structure of the chiral aliphatic amine. The methodology is successfully applied to the synthesis of romneine, a natural benzylisoquinoline.
PB Royal Society of Chemistry
YR 2023
FD 2023-03-13
LK https://hdl.handle.net/10630/29398
UL https://hdl.handle.net/10630/29398
LA eng
NO Fuentes-Ríos, David; Muñoz, Carmen; Díaz-Morilla, Amelia; Sarabia-García, Francisco Ramón; López-Romero, Juan Manuel. Diastereoselective C-alkylation of aldimines, derived from chiral alpha-carbon heteroatom substituted aldehydes, with triethylborane. Application to the synthesis of benzylisoquinolines. RSC Advances 2023, 13, 8976-8984
DS RIUMA. Repositorio Institucional de la Universidad de Málaga
RD 20 ene 2026