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Development of novel organocatalytic cascade reactions and application in organic systheses

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Please use this identifier to cite or link to this item: http://hdl.handle.net/1928/20880

Development of novel organocatalytic cascade reactions and application in organic systheses

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dc.contributor.author Song, Xixi
dc.date.accessioned 2012-07-06T15:54:44Z
dc.date.available 2012-07-06T15:54:44Z
dc.date.issued 2012-07-06
dc.date.submitted May 2012
dc.identifier.uri http://hdl.handle.net/1928/20880
dc.description.abstract The development of new catalytic reactions, particularly synthetically efficient cascade processes for the facile preparation of important molecular architectures, which otherwise are difficult to access via traditional methods, is of considerable significance. Toward this end, my Ph.D. work focuses on developing new organocatalytic reactions and their applications in organic syntheses. A novel direct organocatalytic stereoselective α-arylation methodology has been discovered. The cross-coupling-like products are assembled using simple enals and various brominated aromatic systems, such as p-bromophenols, bromonaphthols and 3-bromoindoles. The products have been applied in the concise photo-syntheses of [α]-annulated carbazoles. Moreover, an unexpected reaction has been identified with aliphatic enals, and fully developed into a new [3+3] formal cycloaddition cascade reaction, and serves as a powerful approach to polysubstituted arenes from simple enals in a highly regio- and chemo-selective fashion. The Diels-Alder reaction of acetylenic aldehydes has been realized for “one-pot” synthesis of polysubstituted salicylaldehyde frameworks that were constructed via an unprecedented aminocatalytic Diels-Alder-retro-Diels-Alder cascade from simple alkynals and 2-pyrones. Furthermore, the use of N-protected 3-hydroxy-2-pyridines as dienes leads to catalytic enantioselective Diels-Alder process without subsequent retro-Diels-Alder reaction. A chiral C2 symmetric organocatalyst is found as an effective promoter for the activation and stereo-control of various substituted alkynals. en_US
dc.language.iso en_US en_US
dc.subject organocatalysis en_US
dc.subject cascade reaction en_US
dc.subject asymmetric catalysis en_US
dc.subject aminocatalysis en_US
dc.subject.lcsh Catalysis.
dc.subject.lcsh Organic chemistry.
dc.subject.lcsh Organic compounds--Synthesis.
dc.subject.lcsh Arylation.
dc.subject.lcsh Alkenes.
dc.subject.lcsh Organobromine compounds.
dc.subject.lcsh Carbazole--Synthesis.
dc.subject.lcsh Diels-Alder reaction.
dc.subject.lcsh Asymmetric synthesis.
dc.title Development of novel organocatalytic cascade reactions and application in organic systheses en_US
dc.type Dissertation en_US
dc.description.degree Chemistry en_US
dc.description.level Doctoral en_US
dc.description.department University of New Mexico. Dept. of Chemistry en_US
dc.description.advisor Wang, Wei
dc.description.committee-member Wang, Wei
dc.description.committee-member Mariano, Patrick
dc.description.committee-member Guo, Hua
dc.description.committee-member Feng, Changjian


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