1616980-04-1Relevant articles and documents
Fluorination Patterning: A Study of Structural Motifs That Impact Physicochemical Properties of Relevance to Drug Discovery
Huchet, Quentin A.,Kuhn, Bernd,Wagner, Bj?rn,Kratochwil, Nicole A.,Fischer, Holger,Kansy, Manfred,Zimmerli, Daniel,Carreira, Erick M.,Müller, Klaus
, p. 9041 - 9060 (2015)
The synthesis of a collection of 3-substituted indole derivatives incorporating partially fluorinated n-propyl and n-butyl groups is described along with an in-depth study of the effects of various fluorination patterns on their properties, such as lipophilicity, aqueous solubility, and metabolic stability. The experimental observations confirm predictions of a marked lipophilicity decrease imparted by a vic-difluoro unit when compared to the gem-difluoro counterparts. The data involving the comparison of the two substitution patterns is expected to benefit molecular design in medicinal chemistry and, more broadly, in life as well as materials sciences.
Total Synthesis of Isodihydrokoumine, (19 Z)-Taberpsychine, and (4 R)-Isodihydroukoumine N4-Oxide
Kerkovius, Jeff K.,Kerr, Michael A.
, p. 8415 - 8419 (2018/07/05)
We report the total synthesis of the natural products isodihydrokoumine and (19Z)-taberpsychine in 11 steps each and (4R)-isodihydrokoumine N4-oxide in 12 steps from commercially available starting materials. The key reactions include an intramolecular [3 + 2] nitrone cycloaddition and Lewis acid mediated cyclizations of a common intermediate to provide the core structures of either taberpsychine or isodihydrokoumine.
Direct use of allylic alcohols for palladium-catalyzed synthesis of 3-allylbenzo[b]thiophenes, benzofurans and indoles in aqueous media
Dhage, Yogesh Daulat,Shirai, Tsukasa,Arima, Miho,Nakazima, Arisa,Hikawa, Hidemasa,Taichi Kusakabe, Isao Azumaya,Takahashi, Keisuke,Kato, Keisuke
, p. 42623 - 42627 (2015/05/27)
Allylative cyclization of (o-alkynylphenyl) (methoxymethyl) sulfides, o-alkynylanilines and o-alkynylphenols catalyzed by π-allyl palladium species generated from simple allylic alcohols is described. 3-Allylbenzo[b]thiophenes, 3-allylindoles and 3-allylb
Rational design of a second generation catalyst for preparation of allylsilanes using the silyl-Heck reaction
McAtee, Jesse R.,Yap, Glenn P. A.,Watson, Donald A.
supporting information, p. 10166 - 10172 (2014/08/05)
Using rational ligand design, we have developed of a second-generation ligand, bis(3,5-di-tert-butylphenyl)(tert-butyl)phosphine, for the preparation of allylsilanes using the palladium-catalyzed silyl-Heck reaction. This new ligand provides nearly complete suppression of starting material alkene isomerization that was observed with our first-generation catalyst, providing vastly improved yields of allylsilanes from simple alkene starting materials. The studies quantifying the electronic and steric properties of the new ligand are described. Finally, we report an X-ray crystal structure of a palladium complex resulting from the oxidative addition of Me3SiI using an analogous ligand that provides significant insight into the nature of the catalytic system.
