57527-55-6Relevant articles and documents
α-Amino acid synthesis via a Cu(II) chiral Lewis acid mediated addition of soft carbon nucleophiles to glycine cation equivalents
Attrill, Rick,Tye, Heather,Cox, Liam R.
, p. 1681 - 1684 (2004)
A new method for the formation of α-amino acid derivatives via Lewis acid mediated additions of soft carbon nucleophiles to carbamate protected glycine cation equivalents is described. A number of derivatives have been prepared in moderate yields and up to 85% ee using a Cu(II)-diamine catalyst combination.
Ruthenium N-Heterocyclic Carbene Complexes for Chemoselective Reduction of Imines and Reductive Amination of Aldehydes and Ketones
Kathuria, Lakshay,Samuelson, Ashoka G.
supporting information, (2020/06/17)
Chemoselective reduction of imines to secondary amines is catalyzed efficiently by tethered and untethered, half-sandwich ruthenium N-heterocyclic carbene (NHC) complexes at room temperature. The untethered Ru-NHC complexes are more efficient as catalysts for the reduction of aldimines and ketimines than the tethered complexes. Using the best untethered complex as a catalyst, electronic and steric demands on the reaction was probed using a series of imines. Chemoselectivity of the catalyst towards imine reduction was tested by performing inter and intramolecular competitive reactions in a variety of ways. The catalyst exhibits a very high TON and TOF under anaerobic conditions.
Tris(2,4,6-trifluorophenyl)borane: An Efficient Hydroboration Catalyst
Lawson, James R.,Wilkins, Lewis C.,Melen, Rebecca L.
supporting information, p. 10997 - 11000 (2017/08/22)
The metal-free catalyst tris(2,4,6-trifluorophenyl)borane has demonstrated its extensive applications in the 1,2-hydroboration of numerous unsaturated reagents, namely alkynes, aldehydes and imines, consisting of a wide array of electron-withdrawing and donating functionalities. A range of over 50 borylated products are reported, with many reactions proceeding with low catalyst loading under ambient conditions. These pinacol boronate esters, in the case of aldehydes and imines, can be readily hydrolyzed to leave the respective alcohol and amine, whereas alkynyl substrates result in vinyl boranes. This is of great synthetic use to the organic chemist.
Stereoselective synthesis of α-alkylidene β-oxo amides by palladium-catalyzed carbonylation
Perrone, Serena,Salomone, Antonio,Caroli, Antonio,Falcicchio, Aurelia,Citti, Cinzia,Cannazza, Giuseppe,Troisi, Luigino
, p. 5932 - 5938 (2015/03/30)
A direct method to obtain α-alkylidene β-oxo amides by the palladium-catalyzed carbonylation of α-chloro ketones in the presence of aromatic imines has been described. The methodology can be applied to a variety of C-aryl imines bearing N-aryl or N-alkyl substituents. The entire process is highly stereoselective and affords the α-alkylidene β-oxo amides only as (Z) isomers. A mechanistic hypothesis involving an acyl-β-lactam intermediate has also been proposed.
