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Record:
=LDR 04178cam a22004333u 4500
=001 3051576
=005 20160427112215.0
=006 m\\f\\d\\\\
=007 he\amu\\bucu
=008 081217s2008\\kina\\smb\\000\0\eng\d
=020 \$a9780494461853
=040 \$aCaOKQ$beng$cCaOKQ
=100 1$aAlessi, Manlio.
=245 10$aSynthetic methods and application based on directed ortho Metalation and Suzuki cross coupling strategies /$cby Manlio Alessi.
=264 \1$aKingston, Ont. :$b[publisher not identified],$c2008.
=300 \$axxxii, 319 leaves :$billustrations (some color)
=336 \$atext$btxt$2rdacontent
=337 \$acomputer$bc$2rdamedia
=338 \$aonline resource$bcr$2rdacarrier
=502 \$aPh.D, Chemistry$bQueen's University$c2008
=504 \$aIncludes bibliographical references.
=520 3$aThe Directed ortho Metalation reaction is described in Chapter 1 of this thesis with particular emphasis on its mechanism and synthetic potential. Chapter 2 contains a review of the DoM (Directed ortho Metalation) of pyridine systems and describes the conditions that allow the one-pot DoM (Directed ortho-Metalation)-Boronation-Suzuki-Miyaura cross coupling of pyridines 2.263a-c, 2.351-2.53 (Table 2.9) bearing several DMGs (Directed Metalation Groups) including the synthetically versatile diethyl amide functionality without incurring into commonly observed self-condensation processes. The method avoids the tedious and uncertain isolation of the intermediate boronic acids while offering rapid access to synthetically valuable arylpyridines (2.354a-s, Table 2.9). Selected aryl pyridine carboxamides were used to demonstrate the DoM-DreM (Directed remote Metalation) nexus that furnishes substituted and isomerically diverse azafluorenones 2.380a-d (Table 2.11) with high regioselectivity. The previous discovery of the anionic O [right arrow] α -vinyl carbamoyl migration of carbamoyl stilbenes stimulated its application in the total synthesis of natural product isoprekinamycin, bearing the unusual diazo group. Chapter 3 of this thesis describes the efficient synthesis of the key stilbene derivative 3.113 and its structural variations whose conversion to the desired naphthols 3.143, 3.144, 3.153 and 3.169 (Table 3.3) is accompanied by extensive decomposition, thus terminating this approach to isoprekinamycin. A modified approach via Z-3.271 (Scheme 3.54) gave the desired naphthyl carbamate intermediates 3.274 and 3.278 (Schemes 3.55 and 3.56, respectively) whose complex DreM reactions prevented the completion of the synthesis but remain under active investigation in our laboratories. Previous studies of the DoM reaction of aryl tetramethyl phosphorodiamidate have shown that unpractical experimental conditions are necessary, thus limiting synthetic application. Chapter 4 of this thesis describes the results concerning the performance of the tetraethyl phosphorodiamidate DMG under standard DoM and DreM conditions, anionic phospha-Fries rearrangement, 1,4 lateral migration, and Suzuki cross coupling which demonstrate synthetic utility and application in synthetic aromatic chemistry.
=533 \$aCopy 2, microfiche.$bOttawa :$cNational Library of Canada,$d[2008] --$e4 microfiches ; 11 x 15 cm. --$f(Canadian theses = Thèses canadiennes)
=538 \$aMode of access: World Wide Web.
=540 \$aThis publication is made available by the authority of the copyright owner solely for the purpose of private study and research and may not be copied or reproduced except as permitted by the copyright laws without written authority from the copyright owner.
=500 \$aGMD: electronic resource.
=653 \$aDirected ortho-Metalation.
=653 \$aPyridines.
=653 \$aPhosphorodiamidate.
=653 \$aIsoprekinamycin.
=653 \$aDirected remote Metalation.
=653 \$aCross coupling.
=653 \$aSuzuki.
=653 \$aAzabiaryls.
=710 2$aQueen's University (Kingston, Ont.).$tTheses (Queen's University (Kingston, Ont.))
=710 2$aQueen's University (Kingston, Ont.).$bDepartment of Chemistry.
=830 \0$aCanadian theses.
=948 \$ac:sb
=902 \$aMARCIVE2013

Record File: eee49a1ef59b1663e0f9a8589f01a024.mrc