54295-56-6Relevant academic research and scientific papers
Reductive coupling between aromatic aldehydes and ketones or imines by copper catalysis
Takeda, Mitsutaka,Mitsui, Atsuhisa,Nagao, Kazunori,Ohmiya, Hirohisa
supporting information, p. 3664 - 3669 (2019/02/14)
The copper-catalyzed reductive coupling of two different carbonyl compounds has been achieved. The reaction of aromatic aldehydes and arylketones with a silylboronate in the presence of a catalytic amount of a CuCl-N-heterocyclic carbene (NHC) complex and a stoichiometric amount of alkoxide base yielded cross-coupled 1,2-diol derivatives. A reaction pathway is proposed that involves the catalytic formation of a nucleophilic α-silyloxybenzylcopper(I) species from the aromatic aldehyde and its subsequent coupling with the arylketone. This process was amenable to asymmetric catalysis. This copper catalyst system also enabled the reductive coupling between aromatic aldehydes and imines.
One-pot synthesis of trisubstituted 1,2-amino alcohols from deprotonated α-amino nitriles
Kison, Coralie,Opatz, Till
experimental part, p. 2740 - 2745 (2009/04/07)
A short synthesis of N,1,2-trisubstituted vicinal amino alcohols by 1,2-addition of deprotonated N-monosubstituted α-amino nitriles to aldehydes and subsequent one-pot reduction of the intermediates with borane-THF is described. This procedure leads to the predominant formation of the anti-configured products. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Stereochemistry of Imino-group Reduction. Part 3. The Hydride Reduction of Achiral Benzil Monoimines
Alcaide, Benito,Lopez-Mardomingo, Carmen,Perez-Ossorio, Rafael,Plumet, Joaquin
, p. 1649 - 1654 (2007/10/02)
The RR,SS:RS,SR ratio of diastereoisomeric amino-alcohols obtained from the lithium aluminium hydride reduction of the monoimines prepared by reaction of benzil and various aliphatic and aromatic achiral amines has been determined.Stereochemical results a
THE STEREOSELECTIVE REDUCTION OF α-AMINODEOXYBENZOIN DERIVATIVES WITH SODIUM BOROHYDRIDE
Alcaide, Benito,Escobar, Gerardo,Gonzalez-Simo, Jose L.,Lopez-Mardomingo, Carmen,Perez-Ossorio, Rafael,Plumet, Joaquin
, p. 2033 - 2036 (2007/10/02)
Total stereoselectivity is observed in the sodium borohydride reduction of α-aminodeoxybenzoins and their hydrochlorides in various hydroxylic solvents.RS-SR isomer (erythro) was the only aminoalcohol obtained.
