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Doctoral Thesis
DOI
10.11606/T.9.2013.tde-01102013-151136
Document
Author
Full name
Ana Dionéia Wouters
E-mail
Institute/School/College
Knowledge Area
Date of Defense
Published
São Paulo, 2013
Supervisor
Committee
Ludtke, Diogo Seibert (President)
Omori, Alvaro Takeo
Santos, Alcindo Aparecido dos
Silva Junior, Luiz Fernando da
Stefani, Helio Alexandre
Title in Portuguese
Carboidratos como matéria-prima para a preparação de substratos quirais: aplicações em catálise enantiosseletiva e processos diastereosseletivos
Keywords in Portuguese
Carboidratos
Síntese assimétrica
Abstract in Portuguese
O presente trabalho descreve o uso de carboidratos como materiais de partida para a preparação de catalisadores quirais e também de substratos quirais. Primeiramente estudos envolvendo a aplicação de amino álcoois derivados de carboidratos na arilação assimétrica de aldeídos, usando ácidos arilborônicos como fontes de grupos arila transferíveis, revelaram que um ligante preparado a partir da D-xilose mostrou-se bastante eficiente e conduziu aos produtos em excelentes rendimentos e altos excessos enantioméricos. Posteriormente a arilação de aldeídos derivados de carboidratos é descrita. Em alguns casos diastereosseletividades maiores que 20:1 foram observadas e a metodologia foi aplicada a síntese total da 7-epi-goniofufurona e análogos.
Title in English
Carbohydrates as starting materials for the preparation of chiral substrates: applications in enantioselective and diastereoselective processes.
Keywords in English
Asymmetric synthesis
Carbohydrates
Abstract in English
The work described herein is centered on the use of carbohydrates as starting materials for the synthesis of chiral ligands and chiral sugar-derivatives. Initially, chiral amino alcohols were studied as ligands for the asymmetric arylation of aldehydes using aryl boronic acids as the source of transferable aryl groups. We found that a chiral ligand derived from D-xylose was very efficient and the desired products were obtained in excellent yields and enantiomeric excesses. In addition, the arylation of sugar-based aldehydes was also studied. In many cases, excellent diastereoselectivities of >20:1 were achieved and the methodology was employed in the total synthesis of 7-epi-goniofufurone and analogues.
 
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Publishing Date
2013-11-18
 
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