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Doctoral Thesis
DOI
https://doi.org/10.11606/T.46.2000.tde-13062024-120953
Document
Author
Full name
Marcelo Aguiar de Araujo
Institute/School/College
Knowledge Area
Date of Defense
Published
São Paulo, 2000
Supervisor
Committee
Comasseto, Joao Valdir (President)
Baader, Josef Wilhelm
Correia, Carlos Roque Duarte
Pilli, Ronaldo Aloise
Simoneli, Fábio
Title in Portuguese
Síntese e aplicações de teluretos vinílicos
Keywords in Portuguese
Compostos orgânicos
Reações Químicas
Abstract in Portuguese
A presente tese relata a preparação de alguns teluretos vinílicos e sua transformação em Z-vinilcianocupratos de ordem superior (Esquema I). (Ver arquivo PDF). Foram estudadas as reações desses cianocupratos com enonas e epóxidos na formação dos respectivos produtos (Esquema II). (Ver arquivo PDF). Enquanto que a reação dos cianocupratos vinílicos com bromoalquinos levou a formação de sistemas enínicos e enediínicos de configuração Z, unidades estruturais presentes em importantes classes de produtos naturais (Esquema III). (Ver arquivo PDF). Foram estudadas as reações de cianocupratos vinílicos Z, derivados de teluretos de Z-vinil tienila e butila com enonas impedidas, comparando-se a reatividade dos cupratos gerados de diferentes formas, na presença e na ausência de BF3. Et2O (Esquema IV). (Ver arquivo PDF). Parte desta tese foi desenvolvida na Universidade de Nottingham, no laboratório do Professor Dr. Nigel Simpkins. Essa parte do trabalho teve como objetivo a síntese de diaminas quirais (Esquema V) (Ver arquivo PDF) e seu uso na funcionalização enantiosseletiva de cetonas pró-quirais (Esquema VI) (Ver arquivo PDF). Essas aminas foram usadas também em tentativas de adições assimétricas 1,4 de cianocupratos vinílicos Z a enonas (Esquema VII). (Ver arquivo PDF).
Title in English
Síntese e aplicações de teluretos vinílicos
Keywords in English
Compostos orgânicos
Reações Químicas
Abstract in English
This thesis describes the preparation of some vinylic tellurides and their transformation into Z-vinylic higher order cyanocuprates (Scheme I). (See files PDF). The reactions of these cuprates with enones and epoxides were studied (Scheme II). (See files PDF). The reaction of vinylcyanocuprates with bromoalkynes generated Z-enynes and Z-enediynes, present in important classes of natural products (Scheme III). (See files PDF). The reaction of Z-vinylcyanocuprates, derived from Z-vinyl-thienyl and butyl tellurides, with hindered enones were studied. The reactivity of the cuprates generated in different ways, in the presence and in the absence of BF3.Et2O was investigated (Scheme IV). (See files PDF). Part of this thesis was developed at the University of Nottigham, under the supervision of Professor Nigel Simpkins. This part of the work dealt with the synthesis of chiral diamines (Scheme V) (See files PDF) and their use in the stereoselective functionalization of pro-chiral ketones (Scheme VI) (See files PDF). These amines were used in attempted assimetric 1,4-addition of Z-cyanocuprates to enones (Scheme VII). (See files PDF).
 
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Publishing Date
2024-06-13
 
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