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Synthesis of β 2,2 ‐Amino Esters via Rh‐Catalysed Regioselective Hydroaminomethylation
Author(s) -
Cunillera Anton,
Ruiz Aurora,
Godard Cyril
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900642
Subject(s) - chemistry , regioselectivity , imine , steric effects , aniline , amine gas treating , cationic polymerization , phosphine , medicinal chemistry , organic chemistry , toluene , ligand (biochemistry) , amino esters , molecular sieve , catalysis , biochemistry , receptor
The synthesis of β 2,2 ‐amino esters was successfully achieved via Rh‐catalysed regioselective hydroaminomethylation of methyl methacrylate with secondary amines using the neutral precursor [Rh(acac)(CO) 2 ]. In this process, the presence of molecular sieves revealed crucial in order to access the final amino ester. For the synthesis of products containing aniline derivatives, the use of the cationic precursor [Rh(COD) 2 ]BF 4 and Me CgPPh phosphine as ligand was necessary in a mixture of toluene/DCE as solvent. Effects of the steric and electronic properties of the amines were observed during this study. Interestingly, poisoning effect of CO in the hydrogenation of the imine intermediate was observed when benzyl amine was used.