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dc.contributor.authorSong, Xixi
dc.date.accessioned2012-07-06T15:54:44Z
dc.date.available2012-07-06T15:54:44Z
dc.date.issued2012-07-06
dc.date.submittedMay 2012
dc.identifier.urihttp://hdl.handle.net/1928/20880
dc.description.abstractThe 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.isoen_USen_US
dc.subjectorganocatalysisen_US
dc.subjectcascade reactionen_US
dc.subjectasymmetric catalysisen_US
dc.subjectaminocatalysisen_US
dc.subject.lcshCatalysis.
dc.subject.lcshOrganic chemistry.
dc.subject.lcshOrganic compounds--Synthesis.
dc.subject.lcshArylation.
dc.subject.lcshAlkenes.
dc.subject.lcshOrganobromine compounds.
dc.subject.lcshCarbazole--Synthesis.
dc.subject.lcshDiels-Alder reaction.
dc.subject.lcshAsymmetric synthesis.
dc.titleDevelopment of novel organocatalytic cascade reactions and application in organic systhesesen_US
dc.typeDissertationen_US
dc.description.degreeChemistryen_US
dc.description.levelDoctoralen_US
dc.description.departmentUniversity of New Mexico. Dept. of Chemistryen_US
dc.description.advisorWang, Wei
dc.description.committee-memberWang, Wei
dc.description.committee-memberMariano, Patrick
dc.description.committee-memberGuo, Hua
dc.description.committee-memberFeng, Changjian


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