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Highly enantioselective organocatalytic addition of aldehydes to N-(phenylmethylene)benzamides: Asymmetric synthesis of the paclitaxel side chain and its analogues
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för fysikalisk kemi, oorganisk kemi och strukturkemi, Avdelningen för fysikalisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
2009 (engelsk)Inngår i: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 15, nr 16, s. 4044-4048Artikkel i tidsskrift (Fagfellevurdert) Published
sted, utgiver, år, opplag, sider
Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA , 2009. Vol. 15, nr 16, s. 4044-4048
Emneord [en]
aldehydes, asymmetric catalysis, (phenylmethylene)benzamides, organocatalysis, taxol
HSV kategori
Forskningsprogram
organisk kemi
Identifikatorer
URN: urn:nbn:se:su:diva-28211DOI: 10.1002/chem.200900078ISI: 000265509700013OAI: oai:DiVA.org:su-28211DiVA, id: diva2:222988
Tilgjengelig fra: 2009-06-10 Laget: 2009-06-10 Sist oppdatert: 2017-12-13bibliografisk kontrollert
Inngår i avhandling
1. Amino acid-catalyzed synthesis of amino acid derivatives: Application and semi-synthesis of Paclitaxel, Docetaxel and their derivatives
Åpne denne publikasjonen i ny fane eller vindu >>Amino acid-catalyzed synthesis of amino acid derivatives: Application and semi-synthesis of Paclitaxel, Docetaxel and their derivatives
2010 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
Abstract [en]

This thesis deals with different applications of organocatalysis, where amino acid derivatives and small peptides are applied as catalysts. First, the development of environmentally friendly aldol reactions, carried out in aqueous media is illustrated. The corresponding β-hydroxy ketones are formed with ee´s up to 99%. Chapter 3 describes the ability of β3-amino acids to selectively catalyze Mannich-type reactions and govern the formation of products with high anti-selectivity (up to >19:1) and ee´s up to 99%. In the following chapter, an amino acid-catalyzed one-pot three component Mannich reaction between dihydroxyacetone and PMP-protected imines, is presented. The corresponding a,a’-dihydroxy-b-aminoketones are obtained in high yields and with 82-95% ee. Next, an aza-Morita-Baylis-Hillman reaction was investigated where L-proline is the catalyst. The reaction proceeds with excellent chemo- and enantioselectivity to give the corresponding compounds in good yields and with 97-99% ee. Finally, the last part describes development of a proline-catalyzed Mannich reation between N-acyl imines and protected α-hydroxyaldehyes, providing access to different α-hydroxy-β-amino acids in good yields and high enantioselctivity (92-99% ee). The obtained amino acids were further applied in the semisynthesis of paclitaxel and docetaxel derivatives.

sted, utgiver, år, opplag, sider
Stockholm: Department of Organic Chemistry, Stockholm University, 2010. s. 73
Emneord
Organocatlysis, amino acids, syntesis, Taxol and Taxotere derivatives
HSV kategori
Forskningsprogram
organisk kemi
Identifikatorer
urn:nbn:se:su:diva-39138 (URN)978-91-7447-091-8 (ISBN)
Disputas
2010-06-11, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16b, Stockholm, 10:00 (engelsk)
Opponent
Veileder
Merknad
At the time of the doctoral defense, the following paper was unpublished and had a status as follows: Paper 7: Manuscript.Tilgjengelig fra: 2010-05-20 Laget: 2010-05-10 Sist oppdatert: 2018-01-12bibliografisk kontrollert

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