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Development of novel organocatalytic cascade reactions and application in organic systheses


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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Title: Development of novel organocatalytic cascade reactions and application in organic systheses
Author: Song, Xixi
Advisor(s): Wang, Wei
Committee Member(s): Wang, Wei
Mariano, Patrick
Guo, Hua
Feng, Changjian
Department: University of New Mexico. Dept. of Chemistry
Subject(s): organocatalysis
cascade reaction
asymmetric catalysis
LC Subject(s): Catalysis.
Organic chemistry.
Organic compounds--Synthesis.
Organobromine compounds.
Diels-Alder reaction.
Asymmetric synthesis.
Degree Level: Doctoral
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.
Graduation Date: May 2012
URI: http://hdl.handle.net/1928/20880

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