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Enantioselective allylation of dienals and their application in tiacumicin synthesis

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Title:
Enantioselective allylation of dienals and their application in tiacumicin synthesis
Title (in czech):
Enantioselektivní allylace dienalů a jejich aplikace v syntéze tiacumicinu
Type:
Dissertation
Author:
Ing. Petr Koukal, Ph.D.
Supervisor:
prof. RNDr. Martin Kotora, CSc.
Opponents:
doc. Ing. Radek Cibulka, Ph.D.
prof. RNDr. Milan Pour, Ph.D.
Thesis Id:
145545
Faculty:
Faculty of Science (PřF)
Department:
Department of Organic Chemistry (31-270)
Study programm:
Organic Chemistry (P1402)
Study branch:
-
Degree granted:
Ph.D.
Defence date:
24/09/2018
Defence result:
Pass
Language:
English
Keywords (in czech):
enantioselektivní reakce, allylace, organická syntéza, tiacumicin
Keywords:
enantioselective reactions, allylations, organic synthesis, tiacumicin
Abstract (in czech):
Stávající metodologie katalytické enantioselektivní allylace aldehydů byly aplikovány na konjugované dienaly a později také na haloakrylaldehydy. Vznikající enantiomerně obohacené homoallylalkoholy byly, často ve vysoké enantio- a diastereomerní čistotě, získány reakcemi katalyzovanými buď komerčními Brønstedovskými kyselinami nebo Lewisovskými bázemi vyvinutými naší laboratoří. Následně byl tento postup rozšířen o krotylace a pentenylace, dosud téměř nepublikované nejen v případě těchto výchozích látek. Použitelnost studovaných reakcí v organické syntéze byla demonstrována na přípravě několika přírodních látek či jejich intermediátů.
Abstract:
The current methodologies of catalytic enantioselective allylation of aldehydes were studied on conjugated dienals and later on haloacrylaldehydes as the substrates. The resulting enantioenriched homoallylalcohols were prepared by reactions promoted either by commercial Brønsted acid catalysts or by Lewis base catalysts developed by our group, often with high enantio- and diastereoselectivities. Subsequently, the methodology was expanded on catalytic enantioselective crotylation and pentenylation reactions, practically unknown not only with these substrates. The applicability of this synthetic approach was demonstrated on preparation of several natural products or their intermediates.
Documents
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Download Text of the thesis Ing. Petr Koukal, Ph.D. 15.74 MB
Download Abstract in czech Ing. Petr Koukal, Ph.D. 72 kB
Download Abstract in english Ing. Petr Koukal, Ph.D. 70 kB
Download Autoreferat / doctoral thesis summary Ing. Petr Koukal, Ph.D. 226 kB
Download Opponent's review doc. Ing. Radek Cibulka, Ph.D. 160 kB
Download Opponent's review prof. RNDr. Milan Pour, Ph.D. 920 kB
Download Defence's report 625 kB