37589-40-5Relevant articles and documents
Highly diastereoselective catalytic Meerwein-Ponndorf-Verley reductions
Yin, Jingjun,Huffman, Mark A.,Conrad, Karen M.,Armstrong III, Joseph D.
, p. 840 - 843 (2007/10/03)
Very practical synthesis of ephedrine analogues in high yields and enantiopurity was realized by a highly diastereoselective Meerwein-Ponndorf- Verley (MPV) reduction of protected α-amino aromatic ketones using catalytic aluminum isopropoxide. The high anti selectivity resulted from the chelation of the nitrogen anion to the aluminum. In contrast, high syn selectivity was obtained with α-alkoxy ketones and other compounds via Felkin-Ahn control.
Nitriles under palladium-catalyzed hydrogenation conditions as substitutes for aldehydes in the reaction with 1,2-amino alcohols: Formation of 1,3-oxazolidines and reductive N-alkylation
Henin, Francoise,Letinois, Stephane,Muzart, Jacques
, p. 7187 - 7190 (2007/10/03)
At room temperature, the presence of hydrogen and catalytic amounts of Pd/C induced the formation of 1,3-oxazolidines from nitriles and 1,2-amino alcohols. The subsequent reductive cleavage of the NC-O bond of these heterocycles occurred under the same conditions. Thus, this methodology provides a new one-pot N-alkylation of 19-amino alcohols using nitriles as reagents with yields up to 98%.
