Index Catalog // ScholarsArchive@OSU

A Pyrone Diels–Alder Approach to Substituted Indoles and Carbazoles and the Synthesis of New Ropinirole Analogues

Creator:: Points, Gary L., III
Abstract:: Aromatic heterocycles are core structural motifs in natural products, pharmaceuticals and biological polymers. Indoles, in particular, represent a significant subclass of aromatic heterocycles, both in terms of sheer numbers, but also in biological and pharmaceutical relevance. As such, new methodologies for the synthesis of indoles represent an important and continually...
Resource Type:: Dissertation
Full Text:: forming the bond (i.e., C–H activation vs cross coupling, etc.). For the sake of clarity in addressing

Stereocontrolled Synthesis of Allenes by Eliminative Cross-Coupling of Carbenoids

Creator:: Cao, Yang
Abstract:: The bimolecular reaction of two carbenoid species resulting in the formation of a carbon-carbon double bond (pi-system), referred to herein as carbenoid eliminative cross-coupling (CEXC), involves a series of three fundamental steps: (i) ate-complex formation (transmetalation), (ii) 1,2-metalate rearrangement, and (iii) beta-elimination. All three steps are stereospecific and so the...
Resource Type:: Dissertation
Full Text:: lithiated carbamate (R)-PhCMe(Li)OCb [Cb = CON(i-Pr)2] to lead, after warming to rt (16 h), to the

Scaffold reactivity and large scale Synthesis of organocatalyzed Yamada-Otani Condensation product and investigation of the synthesis and properties of axially chiral 8,8'-biquinolyls and 8-(naphtha-1-yl)quinolines

Creator:: Banerjee, Somdev
Abstract:: In Part I, (4S,5R)-4,5-dimethyl-4-phenylcyclohex-2-enone (19a) was prepared in 73% yield with high enantio- and diastereo-selectivity (er > 98:2, dr > 20:1) on a multigram scale by a Yamada-Otani condensation between (E)-pent-3-en-2-one and 2-phenylpropanal catalyzed by a sulfonimide derivative of (S)-proline (18, HuaCat®). Synthetically useful transformations of the cyclohexenone product 19a...
Resource Type:: Dissertation
Full Text:: -enolate formation (e.g., LDA, DMPU, MeI, THF, –78 °C, 2 h; 86% yield, dr > 20:1), (b) 1,2-addition of

Stereospecific Synthesis of Stereotriad Motifs and Alkenes Using Enantioenriched sp³-Hybridized Carbenoids

Creator:: Xun, Sun
Abstract:: Enantioenriched sp³-hybridized carbenoid reagents CR1R2MX (X = nucleofuge, M = electrofuge) of different types were investigated for the synthesis of polysubstituted alkyl chains by iterative stereospecific reagent-controlled homologation (StReCH) and for the stereospecific connective synthesis of alkenes by eliminative cross-coupling. In the first part, putative enantioenriched α-chloroalkyllithiums (CHRLiCl) were employed...
Resource Type:: Dissertation
Full Text:: species 6 which by today’s definition is indeed a carbenoid. N Ph H N

Analysis of the mechanism of sulfoxide-lithium exchange and the reactive intermediate in stereospecific reagent-controlled homologation (StReCH)

Creator:: Hoyt, Amanda
Abstract:: The stereospecific reagent-controlled homologation (StReCH) of boronic esters with enantioenriched carbenoid species generated in situ by the addition of organolithium initiators to stereodefined α-chloroalkyl aryl sulfoxides was previously reported. The reaction of an organolithium with an α-chloroalkyl aryl sulfoxide ostensibly generates an α-chloroalkyllithium via sulfoxide-lithium exchange; however, the true nature...
Resource Type:: Masters Thesis
Full Text:: )  7.68-7.55 (4H, m), 7.50-7.41 (6H, m); 13C NMR (700 MHz, CDCl3)  145.8 (2C, 0), 131.3 (2C, 1), 129.5

Synthesis and catalytic applications of derivatives of 7,7'-dihydroxy-8,8'-biquinolyl (azaBINOL)

Creator:: Wang, Chao
Abstract:: The synthesis of axially chiral polyfunctional derivatives of 8,8'-biquinolyl was explored and the catalytic action of appropriate derivative types investigated in three separate processes: (1) the silylcyanation of carbonyl groups and imines, (2) alkylation of a glycine Schiff-base via phase transfer-catalysis, and (3) direct amide bond formation from simple amines...
Resource Type:: Dissertation
Full Text:: coupling (69% yield of 8,8´- biquinolyl), a substrate directed double C–H functionalization via Pd(II

Proteomic approach to the analysis of DNA-binding proteins using mass spectrometry

Creator:: Stapels, Martha Degen
Abstract:: In proteomic studies, separate experimental protocols have been necessary to identify proteins, determine their function, and predict their three-dimensional structure. In this study, a function-based separation of proteins was conceived to fractionate proteins prior to enzymatic digestion. In the initial demonstration of this technique, a DNA substrate was used to...
Resource Type:: Dissertation
Full Text:: ., Auberry, D.L., Battista, J.R., Daly, M.J., Fredrickson, J., Hixson, K.K., Kostandarithes, H., Masselon, C

Part I: Synthesis and evaluation of synosutine as an inhibitor of serotonin, norepinephrine, and dopamine transporters Part II: Asymmetric approach to the tetracyclic core of neomangicol A

Creator:: Juniku, Rajan B.
Abstract:: Part I: Racemic and asymmetric syntheses of a new substance with prospective antidepressant properties were achieved. In vitro assays with synthetic racemates (±)-25 and (±)-26 suggested that the former is a relatively selective inhibitor of serotonin transporter whereas the latter is a more balanced inhibitor of both serotonin and norepinephrine...
Resource Type:: Dissertation
Full Text:: (Fig 4).2 Me3N O O Acetylcholine (1) HO HO NH2 HO HO (R) NH2 OH HO N H NH2 Dopamine (5

Stereoselective synthesis & application of enantioenriched main group α-haloalkyl organometal reagents

Creator:: Emerson, Christopher R.
Abstract:: Sulfoxide-ligand exchange (SLE) and asymmetric halogen-metal exchange (AHME) processes were separately examined for the enantioselective synthesis of functionalized alpha-haloalkylmetal (carbenoid) reagents. Carbenoids derived from SLE were used to effect stereospecific reagent-controlled homologation (StReCH) of boronic esters and those generated via AHME were engaged in Darzens-type chemistry with aldehydes. Abstract for...
Resource Type:: Dissertation
Full Text:: was provided.9,10,11 3 Na Br 2 4 -NaBr H Br 1 Br 3 Na NaOMe MeOH Scheme 1. Fritsch

Aryl acetylene substituent effects : the synthesis and application of biaryls

Creator:: Naffziger, Michael R.
Abstract:: The work described herein details the synthesis and application of biphenyls that probe the effects of hydrogen, Cl / Br, and methyl substituents on the aryl ring of the terminal acetylenic carbon. From this work, we successfully developed the rapid synthesis of phenyl acetylenes in 3-4 steps from inexpensive commercially...
Resource Type:: Masters Thesis
Full Text:: .................................................cyclohexyl DABCO ........................................diazabicyclo[2.2.2]octane DIBAL-H

ScholarsArchive@OSU

A Pyrone Diels–Alder Approach to Substituted Indoles and Carbazoles and the Synthesis of New Ropinirole Analogues

Stereocontrolled Synthesis of Allenes by Eliminative Cross-Coupling of Carbenoids

Scaffold reactivity and large scale Synthesis of organocatalyzed Yamada-Otani Condensation product and investigation of the synthesis and properties of axially chiral 8,8'-biquinolyls and 8-(naphtha-1-yl)quinolines

Stereospecific Synthesis of Stereotriad Motifs and Alkenes Using Enantioenriched sp³-Hybridized Carbenoids

Analysis of the mechanism of sulfoxide-lithium exchange and the reactive intermediate in stereospecific reagent-controlled homologation (StReCH)

Synthesis and catalytic applications of derivatives of 7,7'-dihydroxy-8,8'-biquinolyl (azaBINOL)

Proteomic approach to the analysis of DNA-binding proteins using mass spectrometry

Part I: Synthesis and evaluation of synosutine as an inhibitor of serotonin, norepinephrine, and dopamine transporters Part II: Asymmetric approach to the tetracyclic core of neomangicol A

Stereoselective synthesis & application of enantioenriched main group α-haloalkyl organometal reagents

Aryl acetylene substituent effects : the synthesis and application of biaryls

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