72443-82-4Relevant academic research and scientific papers
Enantioselective CuH-catalyzed anti-markovnikov hydroamination of 1,1-disubstituted alkenes
Zhu, Shaolin,Buchwald, Stephen L.
supporting information, p. 15913 - 15916 (2015/02/19)
Enantioselective synthesis of β-chiral amines has been achieved via copper-catalyzed hydroamination of 1,1-disubstituted alkenes with hydroxylamine esters in the presence of a hydrosilane. This mild process affords a range of structurally diverse β-chiral amines, including β-deuterated amines, in excellent yields with high enantioselectivities. Furthermore, catalyst loading as low as 0.4 mol% could be employed to deliver product in undiminished yield and selectivity, demonstrating the practicality of this method for large-scale synthesis.
Direct catalytic enantioselective α-aminomethylation of aldehydes
Ibrahem, Ismail,Zhao, Gui-Ling,Cordova, Armando
, p. 683 - 688 (2007/10/03)
The direct catalytic asymmetric α-aminomethylation of aldehydes is presented. The chiral amine and amino acid catalyzed reactions between unmodified aldehydes and a formaldehyde-derived imine precursor were fast and proceeded with high chemo- and enantios
Asymmetric Reductions of α,β-Acetylenic Ketones and Acetophenone Using Lithium Aluminum Hydride Complexed with Optically Active 1,3-Amino Alcohols
Cohen, Noal,Lopresti, Rocco J.,Neukom, Christian,Saucy, Gabriel
, p. 582 - 588 (2007/10/02)
Asymmetric reduction of the α,β-acetylenic ketones 9a-f using the freshly prepared complex derived from LiAlH4 and (2S,3R)-(+)-4-(dimethylamino)-3-methyl-1,2-diphenyl-2-butanol (Darvon alcohol; 10) at -70 deg C gives mainly the (R)-carbinols 1a-f in yields of 62-99percent and enantiomeric excesses of 34-90percent.Similar treatment of 9e with the complex formed from LiAlH4 and 11, the enantiomer of 10, affords 2e, a useful intermediate for the synthesis of (2R,4'R,8'R)-α-tocopherol (vitamin E), in 96percent yield and 90percent ee.The optically pure 1,3-amino alcohol ligands 12-16, which are structurally related to 10, were prepared by starting from the known (S)-ether sulfonate 23 and its enantiomer.Reduction of 9a and acetophenone using the LiAlH4-12 complex gives an excess of the corresponding (S)-carbinols 2a (36percent ee) and 27 (60percent ee), respectively.
