60444-44-2Relevant academic research and scientific papers
Synthesis of Mixed Secondary and Tertiary Amines
Ayrapetyan, L. V.,Chukhajian, E. O.,Mkrtchyan, H. S.,Panosyan, H. A.
, p. 353 - 355 (2020/04/17)
Abstract: A one-stage and facile method of synthesis of expensive methyl- and ethyl(allyl)amines, methyl- and ethyl(prop-2-ynyl)amines, and methyl- and ethyl(allyl)(3-phenylprop-2-ynyl)amines is developed. The synthesized amines present practical interest, because some (prop-2-ynyl)amines are used in the therapy cancer.
Enantioselective Carboetherification/Hydrogenation for the Synthesis of Amino Alcohols via a Catalytically Formed Chiral Auxiliary
Buzzetti, Luca,Puri??, Mikus,Greenwood, Phillip D. G.,Waser, Jerome
supporting information, p. 17334 - 17339 (2020/11/02)
Chiral auxiliaries and asymmetric catalysis are the workhorses of enantioselective transformations, but they still remain limited in terms of either efficiency or generality. Herein, we present an alternative strategy for controlling the stereoselectivity of chemical reactions. Asymmetric catalysis is used to install a transient chiral auxiliary starting from achiral precursors, which then directs diastereoselective reactions. We apply this strategy to a palladium-catalyzed carboetherification/hydrogenation sequence on propargylic amines, providing fast access to enantioenriched chiral amino alcohols, important building blocks for medicinal chemistry and drug discovery. All stereoisomers of the product could be accessed by the choice of ligand and substituent on the propargylic amine, leading to a stereodivergent process.
Palladium-Catalyzed Carboxy-Alkynylation of Propargylic Amines Using Carbonate Salts as Carbon Dioxide Source
Greenwood, Phillip D. G.,Waser, Jerome
supporting information, p. 5183 - 5186 (2019/06/10)
A palladium-catalyzed multicomponent reaction of propargylic amines, alkynyl bromides and cesium hydrogen carbonate to access oxazolidinones is reported. In contrast to previous reports, only a slight excess of cesium hydrogen carbonate is used as a surrogate of carbon dioxide. The reaction gives access to oxazolidinones bearing alkyl- and aryl polysubstituted enynes in good yield and very high E stereoselectivity.
Lanthanide-Catalyzed Reversible Alkynyl Exchange by Carbon–Carbon Single-Bond Cleavage Assisted by a Secondary Amino Group
Shao, Yinlin,Zhang, Fangjun,Zhang, Jie,Zhou, Xigeng
supporting information, p. 11485 - 11489 (2016/10/24)
Lanthanide-catalyzed alkynyl exchange through C?C single-bond cleavage assisted by a secondary amino group is reported. A lanthanide amido complex is proposed as a key intermediate, which undergoes unprecedented reversible β-alkynyl elimination followed by alkynyl exchange and imine reinsertion. The in situ homo- and cross-dimerization of the liberated alkyne can serve as an additional driving force to shift the metathesis equilibrium to completion. This reaction is formally complementary to conventional alkyne metathesis and allows the selective transformation of internal propargylamines into those bearing different substituents on the alkyne terminus in moderate to excellent yields under operationally simple reaction conditions.
Synthesis of substituted 2-aminoimidazoles via Pd-catalyzed alkyne carboamination reactions. Application to the synthesis of preclathridine natural products
Zavesky, Blane P.,Babij, Nicholas R.,Wolfe, John P.
supporting information, p. 4952 - 4955 (2015/04/27)
A new method for the synthesis of 2-aminoimidazole products is described. The heterocyclic products are generated in good yields via Pd-catalyzed carboamination reactions of N-propargyl guanidines and aryl triflates. This methodology generates both a C-N
Synthesis of bicyclic guanidines via cascade hydroamination/michael additions of mono- n -acryloylpropargylguanidines
Kwon, Ki-Hyeok,Serrano, Catherine M.,Koch, Michael,Barrows, Louis R.,Looper, Ryan E.
supporting information, p. 6048 - 6051 (2015/01/09)
A cascade silver(I)-catalyzed hydroamination/Michael addition sequence has been developed to deliver highly substituted bicyclic guanidines. This transformation gives rise to geometrically and constitutionally stable ene-guanidines and generates a remote stereocenter with moderate to high diastereoselectivity.
Ln[N(SiMe3)2]3-Catalyzed Cross-Diinsertion of C≡N/C≡C into an N-H Bond: Facile Synthesis of 1,2,4-Trisubstituted Imidazoles from Propargylamines and Nitriles
Hong, Longcheng,Shao, Yinlin,Zhang, Lixin,Zhou, Xigeng
supporting information, p. 8551 - 8555 (2014/07/21)
A lanthanide-catalyzed sequential insertion of C≡N and C≡C into an N-H bond is presented. The convenient reaction, which proceeds under mild conditions, is an efficient method for preparing 1,2,4-trisubstituted imidazoles directly from readily available propargylamines and nitriles.
Regioselective rhodium(II)-catalyzed hydroaminations of propargylguanidines
Gainer, Morgan J.,Bennett, Nitasha R.,Takahashi, Yu,Looper, Ryan E.
supporting information; experimental part, p. 684 - 687 (2011/04/16)
Different than others: Dimeric rhodium(II) carboxylates uniquely catalyze the 6-endo-dig selective hydroamination of propargylguanidines while tranditional π-Lewis acids are typically 5-exo-dig selective (see scheme, oct=octanoate). Furthermore, this repr
Small molecule agonists of the orphan nuclear receptors steroidogenic factor-1 (SF-1, NR5A1) and liver receptor homologue-1 (LRH-1, NR5A2)
Whitby, Richard J.,Stec, Jozef,Blind, Raymond D.,Dixon, Sally,Leesnitzer, Lisa M.,Orband-Miller, Lisa A.,Williams, Shawn P.,Willson, Timothy M.,Xu, Robert,Zuercher, William J.,Cai, Fang,Ingraham, Holly A.
supporting information; experimental part, p. 2266 - 2281 (2011/06/19)
The crystal structure of LRH-1 ligand binding domain bound to our previously reported agonist 3-(E-oct-4-en-4-yl)-1-phenylamino-2-phenyl-cis- bicyclo[3.3.0]oct-2-ene 5 is described. Two new classes of agonists in which the bridgehead anilino group from ou
