490035-78-4Relevant academic research and scientific papers
Selecting double bond positions with a single cation-responsive iridium olefin isomerization catalyst
Camp, Andrew M.,Kita, Matthew R.,Blackburn, P. Thomas,Dodge, Henry M.,Chen, Chun-Hsing,Miller, Alexander J.M.
supporting information, p. 2792 - 2800 (2021/03/01)
The catalytic transposition of double bonds holds promise as an ideal route to alkenes of value as fragrances, commodity chemicals, and pharmaceuticals; yet, selective access to specific isomers is a challenge, normally requiring independent development of different catalysts for different products. In this work, a single cation-responsive iridium catalyst selectively produces either of two different internal alkene isomers. In the absence of salts, a single positional isomerization of 1-butene derivatives furnishes 2-alkenes with exceptional regioselectivity and stereoselectivity. The same catalyst, in the presence of Na+, mediates two positional isomerizations to produce 3-alkenes. The synthesis of new iridium pincer-crown ether catalysts based on an aza-18-crown-6 ether proved instrumental in achieving cation-controlled selectivity. Experimental and computational studies guided the development of a mechanistic model that explains the observed selectivity for various functionalized 1-butenes, providing insight into strategies for catalyst development based on noncovalent modifications.
Enantioselective Olefin Hydrocyanation without Cyanide
Schuppe, Alexander W.,Borrajo-Calleja, Gustavo M.,Buchwald, Stephen L.
supporting information, p. 18668 - 18672 (2019/11/28)
The enantioselective hydrocyanation of olefins represents a conceptually straightforward approach to prepare enantiomerically enriched nitriles. These, in turn, comprise or are intermediates in the synthesis of many pharmaceuticals and their synthetic derivatives. Herein, we report a cyanide-free dual Pd/CuH-catalyzed protocol for the asymmetric Markovnikov hydrocyanation of vinyl arenes and the anti-Markovnikov hydrocyanation of terminal olefins in which oxazoles function as nitrile equivalents. After an initial hydroarylation process, the oxazole substructure was deconstructed using a [4 + 2]/retro-[4 + 2] sequence to afford the enantioenriched nitrile product under mild reaction conditions.
MACROCYCLIC BROAD SPECTRUM ANTIBIOTICS
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Paragraph 00618; 00729, (2018/09/12)
Provided herein are antibacterial compounds, wherein the compounds in some embodiments have broad spectrum bioactivity. In various embodiments, the compounds act by inhibition of bacterial type 1 signal peptidase (SpsB), an essential protein in bacteria. Pharmaceutical compositions and methods for treatment using the compounds described herein are also provided.
Alkenyl substituted bicyclic nucleoside analogues retain nanomolar potency against Varicella Zoster Virus
McGuigan, Christopher,Bidet, Olivier,Derudas, Marco,Andrei, Graciela,Snoeck, Robert,Balzarini, Jan
body text, p. 3025 - 3027 (2009/09/30)
Novel alkenyl substituted aryl bicyclic furano pyrimidines have been prepared and evaluated in vitro against Varicella Zoster Virus (VZV). The para-substituted analogues retain the nanomolar potency we have reported for p-alkyl analogues, while the ortho-
Preparation and Properties of Tertiary p-Alkylarylphosphines containing Straight-chain Alkyl Groups
Franks, Stephen,Hartley, Frank R.
, p. 2233 - 2237 (2007/10/02)
A series of tris(p-alkylaryl)phosphines with straight-chain alkyl groups, P(p-C6H4-CnH2n+1)3 where n=2-9, have been prepared by reaction of phosphorus trichloride with the Grignard reagent derived from the corresponding p-bromoalkylbenzene.When n=2 and 3 the phosphines are crystalline solids, but for n>3 they are viscous oils up to n=9, which is a waxy solid.The phosphines have been characterised by microanalysis, and i.r., 1H and 31P n.m.r., and mass spectrometry.The p-substituted-arylphosphines are more sensitive than triphenylphosphine to air; aerial oxidation converts them exclusively into the corresponding phosphine oxides, in contrast to trialkylphosphines which are oxidised to a complex mixture of products.The complexing ability of the new phosphines (PAr3) is demonstrated by their ready displacement of 1,5-cyclo-octadiene (cod) from (M=Pd and Pt) to yield trans- and cis-, respectively.
