Wykorzystanie pochodnych 5-allilo-5-nitro-1,3-dioksanu w syntezie polihydroksylowych pochodnych piperydyny

Anna Budzińska

Abstract

The aim of this Thesis was to investigate using of 5-allyl-5-nitro-l,3-dioxane derivatives in the synthesis of polyhydroxylated piperidine derivatives. 5-allyl-5-nitro-l,3-dioxane derivatives were prepared from the palladium(O) catalysed C-allylation of the 5-nitro-l,3-dioxane. Methods of synthesis three types polyhydroxylated piperidine derivatives were elaborated. In the first method allyl derivatives in three steps, including intramolecular, 1,3-dipolar cycloaddition, were converted into 7-oxa-l-azabicyclo[2.2.1]heptane derivatives. Catalytic hydrogenation and then deprotection of hydroxyl groups leaded to 2,2-bis(hydroxymethyl)-4-hydroxypiperidines. This method was also employed for the synthesis of 2,2,5,6-tetrakis(hydroxymethyl)-4-hydroxypiperidine derivatives. The other method was employed for synthesis of optically active (3R,4S) 2,2-bis(hydroxymethyl)-3,4-dihydroxypiperidinone. The derivative of 5-allyl-5-nitro-l,3-dioxane, having methoxycarbony] group at the sp2 carbon atom, was submitted to a Sharpless asymmetric dihydroxylation. The diol was then hydrogenated and after deprotection of hydroxyl group optically active \03B4-lactam was obtained.
Diploma typeDoctor of Philosophy
Author Anna Budzińska (FC / DOC)
Anna Budzińska,,
- Department Of Organic Chemistry
Title in PolishWykorzystanie pochodnych 5-allilo-5-nitro-1,3-dioksanu w syntezie polihydroksylowych pochodnych piperydyny
Languagepl polski
Certifying UnitFaculty of Chemistry (FC)
Disciplinechemical engineering / (chemical sciences domain) / (physical sciences)
Defense Date19-10-2001
Supervisor Przemysław Szczeciński (FC / DOC)
Przemysław Szczeciński,,
- Department Of Organic Chemistry

Pages134
Keywords in Polishsynteza organiczna, pochodne piperydyny, piperydyna, prace doktorskie
Abstract in EnglishThe aim of this Thesis was to investigate using of 5-allyl-5-nitro-l,3-dioxane derivatives in the synthesis of polyhydroxylated piperidine derivatives. 5-allyl-5-nitro-l,3-dioxane derivatives were prepared from the palladium(O) catalysed C-allylation of the 5-nitro-l,3-dioxane. Methods of synthesis three types polyhydroxylated piperidine derivatives were elaborated. In the first method allyl derivatives in three steps, including intramolecular, 1,3-dipolar cycloaddition, were converted into 7-oxa-l-azabicyclo[2.2.1]heptane derivatives. Catalytic hydrogenation and then deprotection of hydroxyl groups leaded to 2,2-bis(hydroxymethyl)-4-hydroxypiperidines. This method was also employed for the synthesis of 2,2,5,6-tetrakis(hydroxymethyl)-4-hydroxypiperidine derivatives. The other method was employed for synthesis of optically active (3R,4S) 2,2-bis(hydroxymethyl)-3,4-dihydroxypiperidinone. The derivative of 5-allyl-5-nitro-l,3-dioxane, having methoxycarbony] group at the sp2 carbon atom, was submitted to a Sharpless asymmetric dihydroxylation. The diol was then hydrogenated and after deprotection of hydroxyl group optically active \03B4-lactam was obtained.
Thesis file
Budzinska_Anna_wykorzystanie.pdf 4.99 MB
Citation count*4 (2015-07-23)

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