Index Catalog // ScholarsArchive@OSU

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:: Exploiting SLE to generate scalemic carbenoids, the Blakemore group successfully demonstrated proof-of

Catalytic desymmetrization of D₂d̳-symmertic proprochiral tetrasubstituted biphenyl compounds: a novel approach to the synthesis of axially chiral C₂-symmetric molecules

Creator:: Gunderson, Jeremey Tyson
Abstract:: Many D2d-symmetric 2,2',6,6'-tetrasubstituted biphenyls are readily prepared via net oxidative dimerization of appropriate 1,3-disubstituted benzenes. Conversion of such proprochiral compounds to useful C2-symmetric chiral biphenyls requires formal replacement of two substituents on opposing aryl ring units with alternate groups. This under exploited desymmetrization tactic has been demonstrated for the generation...
Resource Type:: Masters Thesis
Full Text:: Abstract approved: Paul R. Blakemore Many D2d-symmetric 2,2',6,6'-tetrasubstituted biphenyls are

Atropisomeric 8,8'-biquinolyl derivatives : synthesis, properties and applications

Creator:: Milicevic, Selena D.
Abstract:: 7,7'-Dihydroxy-8,8'-biquinolyl (azaBINOL) was prepared from 7-hydroxyquinoline via N,N-dimethyl O-quinol-7-yl carbamate by directed ortho-metallation followed by FeCl₃-mediated oxidative coupling of the 8-lithioquinoline intermediate. Saponification of the resulting dicarbamate provided crystalline (±)-azaBINOL in 56% overall yield. 6,6'-Bis(dimethylaminocarbonyl)-7,7'-dihydroxy-8,8´-biquinolyl was prepared from the same dicarbamate by a double anionic-Fries rearrangement in 43% yield. 7,7'-Bis(diethylamino-carbonyloxy)-6,6'-diiodo-8,8´-biquinolyl...
Resource Type:: Dissertation
Full Text:: Paul R. Blakemore 7,7´-Dihydroxy-8,8´-biquinolyl (azaBINOL) was prepared from 7-hydroxyquinoline

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:: Paul R. Blakemore The bimolecular reaction of two carbenoid species resulting in the formation

Precursor-directed Biosynthesis and Total Synthesis of Aniline-containing Natural Products from the Endophytic Fungus Chalara sp. 6661

Creator:: Khoshbakht, Mahsa
Abstract:: Chalaniline A, an unusual xanthone-like aminofulvene with modest cytotoxicity, and chalaniline B [1-anilino-2,8-dihydroxy-3-(hydroxymethyl)xanthone], an antibacterial aminoxanthone, were previously isolated by Loesgen and coworkers from vorinostat-treated Chalara sp. 6661. Of note, the anilino moiety found within both chalaniline structures originates from biotransformation of the HDAC inhibitor vorinostat (SAHA, suberanilohydroxamic acid) by...
Resource Type:: Dissertation
Full Text:: Endophytic Fungus Chalara sp. 6661 Abstract approved: Paul R. Blakemore Chalaniline A, an

Total Synthesis of Isotopologues of Xanthohumol and its Congeners for Biological Studies

Creator:: Plagmann, Layhna S.
Abstract:: Xanthohumol [XN, (E)-6´-methoxy-3´-(3-methylbuten-2-yl)-2´,4´,4´´-trihydroxychalcone], the principal prenylated chalcone from hops, and its 2,3-dihydro- (DXN) and O6-desmethyl-2,3-dihydro- (DDXN) congeners, are of potential utility for the amelioration of metabolic syndrome; however, their complex bioactivity profiles cannot be properly studied and understood without access to appropriately produced synthetic materials. In the first part of...
Resource Type:: Masters Thesis
Full Text:: expresses sincere appreciation to the following people: Prof. Paul R. Blakemore, for his outstanding

Development of Carbenoid Eliminative Cross-coupling for the Stereocontrolled Synthesis of Trisubstituted Alkenyl Moieties Within Styrenes and 1,3-Dienes

Creator:: Tanpure, Subhash D.
Abstract:: Traditional approaches for the direct preparation of alkenes are unable to fully control either the stereochemical configuration of the carbon-carbon double bond or else the regiochemistry of the substituents surrounding it. The recently introduced concept of carbenoid eliminative cross-coupling (CEXC) offers a remedy to these deficiencies by providing for a...
Resource Type:: Dissertation
Full Text:: : ______________________________________________________ Paul R. Blakemore Traditional approaches for the direct preparation of alkenes are

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:: Abstract approved: Paul R. Blakemore In Part I, (4S,5R)-4,5-dimethyl-4-phenylcyclohex-2-enone

Development of Methods for Stereoselective Carbon-Carbon Bond Formation

Creator:: Wu, Zhenhua
Abstract:: Three distinct methods to achieve the stereoselective synthesis of carbon-carbon bonds were investigated, encompassing: (i) the formation of axially chiral biaryl molecules by enantioselective Suzuki cross-coupling, (ii) the synthesis of α-phenylalkylboronic esters by enantioselective chain extension, and (iii) the stereospecific synthesis of alkenes by eliminative cross-coupling of enantioenriched sp³-hybridized carbenoids....
Resource Type:: Dissertation
Full Text:: : ______________________________________________________ Paul R. Blakemore Three distinct methods to achieve the stereoselective synthesis 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:: : ______________________________________________________ Paul R. Blakemore Enantioenriched sp3-hybridized carbenoid reagents CR1R2MX (X

ScholarsArchive@OSU

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

Catalytic desymmetrization of D₂d̳-symmertic proprochiral tetrasubstituted biphenyl compounds: a novel approach to the synthesis of axially chiral C₂-symmetric molecules

Atropisomeric 8,8'-biquinolyl derivatives : synthesis, properties and applications

Stereocontrolled Synthesis of Allenes by Eliminative Cross-Coupling of Carbenoids

Precursor-directed Biosynthesis and Total Synthesis of Aniline-containing Natural Products from the Endophytic Fungus Chalara sp. 6661

Total Synthesis of Isotopologues of Xanthohumol and its Congeners for Biological Studies

Development of Carbenoid Eliminative Cross-coupling for the Stereocontrolled Synthesis of Trisubstituted Alkenyl Moieties Within Styrenes and 1,3-Dienes

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

Development of Methods for Stereoselective Carbon-Carbon Bond Formation

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

Limit your search

Academic Affiliation

Advisor

Commencement Year

Committee Member

Creator

Contributor

Date

Decade

Degree Field

Degree Level

Degree Name

Language

License

Non-Academic Affiliation

Peer Reviewed

Resource Type

Rights Statement

Subject

Search Constraints

Search Results

Limit your search