184110-37-0Relevant articles and documents
Phosphane ligands with two binding sites of differing hardness for enantioselective Grignard cross coupling
Terfort, Andreas,Brunner, Henri
, p. 1467 - 1479 (1996)
A series of new, chiral phosphanes is presented, individual members of which were designed to serve as ligands in transition-metal mediated asymmetric Grignard cross coupling reactions. These ligands are characterized by a side chain containing one or two oxygen atoms with the capacity to act as binding sites for the incoming Grignard reagent. A number of structural parameters for the compounds was varied to learn about the reaction mechanism. Most of the ligands were tested in two cross coupling reactions, the formation of 3-phenylbut-1-ene and of 2,2′-dimethyl-1,1′-binaphthyl, respectively. Although both systems gave modest enantiomeric excesses it was not possible to make a comparison of their respective abilities.
Novel synthesis of chiral, enantiomerically pure thiodiglycols and diglycols
Christoffers, Jens,Roessler, Ulrich
, p. 2349 - 2357 (2007/10/03)
Natural α-hydroxy acids have been converted in a sequence of O- protection, reduction, O-activation, thioether and ether formation and deprotection to chiral, non-racemic β,β'-dihydroxy thioethers 1a, 1b and ether 1c. Overall yields are excellent (75%). In an attempt to synthesize the respective dihydroxy ether 1d derived from mandelic acid 1,3-dioxolane derivatives 7 were obtained.
SYNTHESIS OF AN ORALLY ACTIVE PAF ANTAGONIST OF THE N-PENTADIENAMIDE CLASS
Manchand, Percy S.,Schwartz, Alan,Wolff, Steven,Belica, Peter S.,Madan, Pradeep,et al.
, p. 1351 - 1369 (2007/10/02)
The PAF antagonist -5-(4-methoxyphenyl)-N--2,4-decadienamide (2) was synthesized from (S)-α-methyl-3-pyridinebutanol (14), which was obtained either from ethyl lactate or by enantioselective kinetic hydrolysis of its racemate using the lipase derived from Pseudomonas cepacia (syn.P. fluorescens).Mesylation of 14, followed by azide displacement and hydrogenation, produced amine (7), which was coupled with the p-nitrophenol ester (8) to give 2.The direct coupling of (E,E)-5-(4-methoxyphenyl)-2,4-decadienoic acid (27) with azide(24) in the presence of tri-n-butylphosphine also gave 2.Acid (27) was prepared by a vinylogous Reformatsky reaction between ketone (25) and methyl 4-bromocrotonate.