164362-55-4Relevant academic research and scientific papers
Synthesis of β-lactams and β-aminoesters via high intensity ultrasound-promoted Reformatsky reactions
Ross, Nathan A.,MacGregor, Robert R.,Bartsch, Richard A.
, p. 2035 - 2041 (2004)
Reformatsky reactions of an imine, an α-bromoester, zinc dust and a catalytic amount of iodine in dioxane under high intensity ultrasound (HIU) irradiation from an ultrasonic probe are explored. A series of 16 aldimines with varying electronic demands is
Photo-induced reductive cross-coupling of aldehydes, ketones and imines with electron-deficient arenes to construct aryl substituted alcohols and amines
Liu, Zan,Nan, Xiaolei,Lei, Tao,Zhou, Chao,Wang, Yang,Liu, Wenqiang,Chen, Bin,Tung, Chenho,Wu, Lizhu
, p. 487 - 494 (2018/03/22)
Umpolung reactions of C=X bonds (X = O, N) are valuable ways of constructing new C–C bonds, which are sometimes difficult to be constructed using traditional synthetic pathways. Classical polarity inversion of C=X bonds (X = O, N) usually requires air or moisture-sensitive and strong reducing agents, which limit the feasibility of substrate scope. Herein we describe a photo-induced reductive cross-coupling reaction of aldehydes, ketones and imines with electron-deficient arenes (aromatic nitriles) using fac-Ir(ppy)3 as a photocatalyst and diisopropylethylamine (DIPEA) as a terminal reductant under visible light irradiation. Mild conditions and high yields mean that this new polarity inversion strategy can be used with aryl-substituted alcohols and amines. Spectroscopic studies and control experiments have demonstrated the oxidative quenching of Ir(ppy)3* by electron-deficient arenes involved in the key step for the C–C bond formation.
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.
Nonradical zinc-barbier reaction for diastereoselective synthesis of vicinal amino alcohols
Keinicke, Lise,Fristrup, Peter,Norrby, Per-Ola,Madsen, Robert
, p. 15756 - 15761 (2007/10/03)
A new protocol for the synthesis of vicinal amino alcohols is described. The method employs a Barbier-type reaction between an imine and 3-benzoyloxyallyl bromide in the presence of zinc metal. The addition products are debenzoylated to afford amino alcohols in good yields and with diastereomeric ratios greater than 85:15 in favor of the anti isomer. A Hammett study has been performed which strongly indicates that the allylation does not follow a radical mechanism, but instead an organometallic reagent is formed which subsequently reacts with the imine. A computational study based on this mechanism reproduces the observed diastereoselectivity with high accuracy, but only when a sufficiently large portion of the substrate is included.
Oxidative carbon-carbon bond cleavage reaction of 1,2-diamines and 1,2-amino alcohols under an oxygen atmosphere
Shimizu, Makoto,Makino, Hiroaki
, p. 8865 - 8868 (2007/10/03)
Under an atmosphere of oxygen 1,2-diamines underwent clean oxidative cleavage in the presence of BF3·OEt2 to give imines in good to excellent yields. 1,2-Amino alcohols were also cleaved under the same conditions to give imines and a
