82215-75-6Relevant academic research and scientific papers
High Diastereoselectivity in the Reaction of α-Aminonitriles bearing an (S)-(+)-2-Methoxymethylpyrrolidine Group with Grignard Reagents
Maigrot, Nicole,Mazaleyrat, Jean-Paul,Welvart, Zoltan
, p. 40 - 41 (1984)
(S)-(+)-2-Methoxymethylpyrrolidine induces high diastereoselectivities (80percent diastereoisomeric excess) in the reaction of α-aminonitriles with Grignard reagents.
Nickel catalysed coupling of allylamines and boronic acid
Trost, Barry M.,Spagnol, Michel D.
, p. 2083 - 2096 (2007/10/02)
Allylamines function as substrates for cross-coupling with boronic acids in the presence of nickel(0) catalysts rather than palladium(0) catalysts.Aryl-, vinyl- and methyl-boronic acids function well.With vinyl derivatives, E-isomers couple more efficiently than Z-isomer and both fully retain the geometrical integrity.Methylations preferably employ the boronic esters like 2-methyl-1,3,2-benzodioxaborole or 2-methyl-1,3,2-dioxaborolane rather than methylboronic acid.The stereochemistry of the reaction involves a net inversion with respect to the allylamine.The regioselectivity is a function of ligand.Generally, sterically bulky donor phosphines promote new C-C bond formation at the less substituted position.Bidentate ligands, notably 1,1'-binaphthyl-2,2'-ylbis(diphenylphosphinite) (BINAPO), promote new C-C bond formation at the more substituted allyl terminus.The amines appear to be the preferred partner compared to allyl alcohols and esters with the boronic acids and give higher stereospecificity.
C-C - CONNECTIVE SYNTHESIS OF α-DIALKYLAMINO - KETONES FROM ALDEHYDES AND SEC.-AMINES
Enders, Dieter,Lotter, Hermann
, p. 639 - 642 (2007/10/02)
A simple and efficient 3 - step synthesis of α-dialkylamino - ketones 3 starting from aldehydes and sec.-amines is described.The unsymmetrically aminoketones are obtained as pure regioisomers via reaction of metalated α-aminonitriles 1 with aldehydes, followed by thermal HCN-elimination/tautomerization.
