Journal
JOURNAL OF ORGANOMETALLIC CHEMISTRY
Volume 653, Issue 1-2, Pages 252-260Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/S0022-328X(02)01271-8
Keywords
cross-coupling; anilinium hypophosphite; phosphinic acid; palladium catalysis; GABA analogs
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Alkenyl bromides and triflates undergo palladium-catalyzed cross-coupling with anilinium hypophosphite to afford monosubstituted phosphinates (salts of alkenylphosphonous acids). The reaction is an extension of our previously reported methodology for the synthesis of aryl- and benzyl-phosphonous acids. Our preliminary results show that the best reaction conditions are observed with Pd(OAc)(2)/dppp as a catalyst, in refluxing benzene or tetrahydrofuran. This novel P-C bond forming reaction is applied to the synthesis of (1,2,3,6-tetrahydropyridin-4-yl)-methylphosphinic acid (TPMPA), a selective competitive antagonist for GA-BA(C) receptors. The divergent synthesis proceeds through protected (1,2,3,6-tetrahydropyridin-4-yl)-phosphinic acid, a previously unknown isoguvacine-like GA-BA analog. This synthetic intermediate is also an ideal precursor to other biologically interesting GABA analogs. (C) 2002 Elsevier Science B.V. All rights reserved.
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