27831-78-3Relevant academic research and scientific papers
SUBSTITUTED PHENYL ALKANOIC ACID COMPOUNDS AS GPR120 AGONISTS AND USES THEREOF
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, (2016/02/09)
The present invention relates to substituted phenyl alkanoic acid compounds designated as the compound of Formula (I) (as described herein) or a tautomer, a stereoisomer, a geometrical isomer, a pharmaceutically acceptable salt, a pharmaceutically acceptable solvate, a prodrug, a polymorph, an N-oxide, a S-oxide or a carboxylic acid isostere thereof; which are GPR120 agonists. The present invention also relates to a pharmaceutical composition of compound of Formula (I) for the treatment of diseases or discorder mediated by GPR120.
Enantioselective synthesis of cis-1,2-disubstituted cyclopentanes and cyclohexanes by Suzuki-Miyaura cross-coupling and iridium-catalyzed asymmetric hydrogenation
Schumacher, Andreas,Schrems, Marcus G.,Pfaltz, Andreas
, p. 13502 - 13509 (2012/01/05)
A series of 1,2-disubstituted cyclohexene derivatives was prepared through Suzuki-Miyaura cross-coupling of 2-bromo-1-cyclohexenecarbaldehyde or 2-carbomethoxy-1-cyclohexen-1-yl triflate with arylboronates. These tetra-substituted cyclic alkenes were subjected to Ir-catalyzed asymmetric hydrogenation. In this way cis-1-methoxymethyl-2-arylcyclohexanes were obtained in high yield with excellent enantio- and diastereoselectivities (up to >99%ee, >99%cis) by using phosphinomethyloxazolines as ligands. Asymmetric hydrogenation of analogous cyclopentene derivatives, prepared by Suzuki-Miyaura cross-coupling, proved to be more difficult and proceeded with lower enantioselectivities of up to 88%ee. The synthetic potential of this cross-coupling/asymmetric-hydrogenation strategy was demonstrated by an enantioselective route to chiral hexahydrofluorenones. Alkene interest: Starting from arylboronates, a variety of cyclic, tetra-substituted olefins was prepared by Suzuki-Miyaura cross-coupling (see scheme). Subsequent Ir-catalyzed asymmetric hydrogenation with phosphanylmethyloxazoline ligand complexes led to cis-disubstituted cycloalkane derivatives in high yield and excellent enantio- and distereoselectivities. Copyright
Auxiliary-directed peroxidation of 1,4-dienes
Dussault, Patrick H.,Anderson, Todd A.,Hayden, Michael R.,Koeller, Kevin J.,Jason Niu
, p. 12381 - 12398 (2007/10/03)
The addition of singlet oxygen (1O2) to the proximal alkene of auxiliary-tethered 1,4-dienes and the addition of triplet oxygen 3O2) to the proximal position of the corresponding pentadienyl radicals both produce conjugated diene hydroperoxides in moderate to high diastereomeric excess. Negligible stereoselection is observed for additions of 1O2 to the distal alkene of Z,Z-heptadienes due to the lack of control of alkene conformation. Despite evidence for the intermediacy of highly constrained pentadienyl radicals, poor diastereoselection is also observed for distal addition of 3O2. The extent of olefin isomerization observed during radical oxygenations can be correlated with steric constraints on the intermediate pentadienyl and peroxyl radicals and may be relevant to literature reports of olefin isomerization during enzymatic oxygenations of unnatural fatty acids.
Electrophilic Additions to the Bicyclobutane System of 1-Phenyl- and 1-(4-Anisyl)tricyclo2,7>heptane: Acid-Catalyzed Reactions with Water and Methanol, Addition of Acetic Acid, and Oxymercuration
Christl, Manfred,Gerstner, Erwin,Kemmer, Ralf,Llewellyn, Gareth,Bentley, T. William
, p. 367 - 380 (2007/10/02)
1-(4-Anisyl)tricyclo2,7>heptane (37) was prepared from 1-(4-anisyl)cyclohexene, tetrabromomethane, and methyllithium in a one-pot reaction.Starting from 37 and the analogous phenyl compound 19, the oxymercuration/demercuration sequence
