76353-13-4Relevant academic research and scientific papers
Enantioselective addition of dimethylzinc to aldehydes catalyzed by N-substituted mandelamide-Ti(IV) complexes
Blay, Gonzalo,Fernandez, Isabel,Hernandez-Olmos, Victor,Marco-Aleixandre, Alicia,Pedro, Jose R.
, p. 1953 - 1958 (2005)
Amides derived from (S)-(+)-mandelic acid in the presence of titanium isopropoxide catalyze the enantioselective addition of dimethylzinc to aromatic aldehydes with good yields and ee up to 90%.
Catalytic asymmetric transfer hydrogenation of ketones using [Ru(p-cymene)Cl2]2 with chiral amino alcohol ligands
Deshpande, Sudhindra H.,Kelkar, Ashutosh A.,Gonnade, Rajesh G.,Shingote, Savita K.,Chaudhari, Raghunath V.
experimental part, p. 231 - 238 (2011/01/12)
Catalytic asymmetric transfer hydrogenation of aromatic alkyl ketones has been investigated using [Ru(p-cymene)Cl2]2 and new derivatives of β-amino alcohols synthesized from (S)-(-)-lactic acid and mandelic acid as ligands. Chiral secondary alcohols were obtained with good to excellent conversion (60-90%) and moderate to good enantioselectivities (40-86%).
STEREOCHIMIE DE LA REDUCTION ELECTROCHIMIQUE D'α-CETOAMIDES OPTIQUEMENT ACTIVES I. ELECTROREDUCTION DE LA S(-) N-(α-METHYLBENZYL)BENZOYLFORMAMIDE
Boulmedais, Ali,Jubault, Michel,Tallec, Andre
, p. 610 - 617 (2007/10/02)
Electrochemical reduction of the title compound has been investigated in hydro-alcoholic medium, at a mercury cathode.Polarographic study shows adsorption of the substrate in very acidic medium (pH 5.5.Controlled potential electrolyses give the corresponding mandelamide in a quasi-quantitative yield; titration of the mixture of the two epimers is achieved by proton NMR at 300 MHz.In very acidic medium, preferential formation of the RS mandelamide is observed (higher optical yield:12.5percent).On the contrary, SS mandelamide is generally the main stereoisomerin acetic or ammoniacal buffer; however, when electroreductions are carried out at very cathodic potentials, again preferential formation of the RS epimer is observed.Stereochemistry of the reduction is explained taking into account conformations of the starting molecule and protonation of the carbanion resulting from a 2 electron reduction.
Scope and Limitations of the TiCl4-Mediated Additions of Isocyanides to Aldehydes and Ketones with Formation of α-Hydroxycarboxylic Acid Amides
Seebach, Dieter,Adam, Geo,Gees, Thomas,Schiess, Martin,Weigand, Wolfgang
, p. 507 - 518 (2007/10/02)
The adducts obtained from TiCl4 and achiral (8-12) or chiral, nonracemic (13-22) isocyanides are combined with aldehydes (aromatic or aliphatic) and ketones (acetone, cyclohexanone, acetophenone) to give, after aqueous workup, α-hydroxyamides (27-55) .The transformation is compatible with a variety of functional groups (aromatic and heterocyclic rings, amino, ether, ester, and amido groups, halides, and phosphonate substituents).The yields range from 14 to over 95percent (with the lower values in the case of more highly functionalised isocyanides).No diastereoselectivity is observed with chiral isocyanides.If the R groups of the isocyanide (R-NC) form a rather stable cation (t-alkyl or benzylic), cyanohydrins may result from the reaction, rather than the N-substituted α-hydroxyamides (see Scheme 2).
The Preparation and Absolute Configuration of the Optically Active Forms of the Diastereoisomers of 2-(1-Phenylethyl)amino-1-phenylethanol and Their Use as Chiral Auxiliaries in the Asymmetric Reduction of Acetophenone with Modified Lithium Aluminium Hydrides
Garry, Scott W.,Neilson, Douglas G.
, p. 601 - 606 (2007/10/02)
(1S,2S)-(-)-2-(1-Phenylethyl)amino-1-phenylethanol (4b) (α-form) and the (1S,2R)-(+)-diastereoisomer (4f) (β-form) were prepared by lithium aluminium hydride reduction of the optically active amides derived from the appropriate mandelic acids and 1-phenylethylamines.The preparative methods give the absolute stereochemistry.The aminoethanols (4) were used along with the lower alcohols to prepare chirally modified lithium aluminium hydrides which were in turn used to reduce acetophenone.The optical yields varied, giving at best, under low temperature conditions and use of a 25 percent optical yield.
